NPASS Compound

Structure

CID270699 OpenBabel06191716072D 28 28 0 0 0 0 0 0 0 0999 V2000 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 26 2 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.28
Volume:	437.082
LogP:	7.494
LogD:	5.345
LogS:	-7.04
# Rotatable Bonds:	16
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	2.089
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.655
MDCK Permeability:	1.8263632227899507e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	97.62890625%
Volume Distribution (VD):	1.445
Pgp-substrate:	1.565868616104126%

ADMET: Metabolism

CYP1A2-inhibitor:	0.134
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.699
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.36
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.116
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	9.241
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.003
Drug-inuced Liver Injury (DILI):	0.367
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.933
Carcinogencity:	0.334
Eye Corrosion:	0.02
Eye Irritation:	0.98
Respiratory Toxicity:	0.052

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC270699

Natural Product ID:	NPC270699
*Common Name:**	Bis(6-Methylheptyl) Benzene-1,2-Dicarboxylate
IUPAC Name:	bis(6-methylheptyl) benzene-1,2-dicarboxylate
Synonyms:
Standard InCHIKey:	IJFPVINAQGWBRJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H38O4/c1-19(2)13-7-5-11-17-27-23(25)21-15-9-10-16-22(21)24(26)28-18-12-6-8-14-20(3)4/h9-10,15-16,19-20H,5-8,11-14,17-18H2,1-4H3
SMILES:	CC(CCCCCOC(=O)c1ccccc1C(=O)OCCCCCC(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3186540
PubChem CID:	33934
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	seed	n.a.	PMID[11540412]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[12880307]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Stems	n.a.	n.a.	PMID[17663584]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[18186611]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25900014]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Steamed Roots	n.a.	n.a.	PMID[26200131]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26359402]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14105.3	Panax pseudo-ginseng wall. var. notoginseng (burk.) hoo et tseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28251	Typha orientalis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	7

Activity Type	# Activity
Individual Protein	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	5430.3	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	27216	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	26973.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12048.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	60385.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54303	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38443.6	nM	PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC270699 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	1177
0.2-0.3	2769
0.3-0.4	7884
0.4-0.5	11878
0.5-0.6	12358
0.6-0.7	5538
0.7-0.8	750
0.8-0.85	46
0.85-0.9	23
0.9-0.95	7
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC82899
0.9903	High Similarity	NPC1082
0.9903	High Similarity	NPC305912
0.9806	High Similarity	NPC196246
0.9806	High Similarity	NPC93084
0.9806	High Similarity	NPC214067
0.9806	High Similarity	NPC251854
0.9709	High Similarity	NPC10251
0.9709	High Similarity	NPC17417
0.9612	High Similarity	NPC56493
0.9515	High Similarity	NPC119271
0.9439	High Similarity	NPC153053
0.9429	High Similarity	NPC174099
0.932	High Similarity	NPC31786
0.9259	High Similarity	NPC307651
0.9252	High Similarity	NPC321852
0.9159	High Similarity	NPC260818
0.8972	High Similarity	NPC469636
0.8972	High Similarity	NPC265407
0.8972	High Similarity	NPC83628
0.8972	High Similarity	NPC85493
0.8932	High Similarity	NPC146351
0.8857	High Similarity	NPC301943
0.8857	High Similarity	NPC474365
0.8857	High Similarity	NPC89886
0.8835	High Similarity	NPC225060
0.8835	High Similarity	NPC35448
0.8835	High Similarity	NPC78701
0.8829	High Similarity	NPC210092
0.8762	High Similarity	NPC45613
0.8738	High Similarity	NPC249912
0.8738	High Similarity	NPC92754
0.8738	High Similarity	NPC276775
0.8649	High Similarity	NPC128368
0.8636	High Similarity	NPC474157
0.8636	High Similarity	NPC210089
0.8611	High Similarity	NPC37622
0.8611	High Similarity	NPC30594
0.8571	High Similarity	NPC325497
0.8544	High Similarity	NPC130398
0.8534	High Similarity	NPC473243
0.8519	High Similarity	NPC209632
0.8519	High Similarity	NPC269457
0.8505	High Similarity	NPC60679
0.8491	Intermediate Similarity	NPC42211
0.8491	Intermediate Similarity	NPC70624
0.8468	Intermediate Similarity	NPC167504
0.8462	Intermediate Similarity	NPC50872
0.8426	Intermediate Similarity	NPC114594
0.8421	Intermediate Similarity	NPC149691
0.8396	Intermediate Similarity	NPC203925
0.8396	Intermediate Similarity	NPC118343
0.8393	Intermediate Similarity	NPC79496
0.8347	Intermediate Similarity	NPC169913
0.8319	Intermediate Similarity	NPC272524
0.8318	Intermediate Similarity	NPC282895
0.8288	Intermediate Similarity	NPC269023
0.8288	Intermediate Similarity	NPC99846
0.8288	Intermediate Similarity	NPC474364
0.8264	Intermediate Similarity	NPC275576
0.8264	Intermediate Similarity	NPC476599
0.8246	Intermediate Similarity	NPC237366
0.8246	Intermediate Similarity	NPC308744
0.8241	Intermediate Similarity	NPC188895
0.8182	Intermediate Similarity	NPC295664
0.8182	Intermediate Similarity	NPC246166
0.8174	Intermediate Similarity	NPC306740
0.8174	Intermediate Similarity	NPC474685
0.8174	Intermediate Similarity	NPC474095
0.8158	Intermediate Similarity	NPC161611
0.8142	Intermediate Similarity	NPC476003
0.8136	Intermediate Similarity	NPC204784
0.8131	Intermediate Similarity	NPC229242
0.813	Intermediate Similarity	NPC51448
0.813	Intermediate Similarity	NPC115797
0.8115	Intermediate Similarity	NPC121272
0.8087	Intermediate Similarity	NPC474363
0.8087	Intermediate Similarity	NPC196075
0.8087	Intermediate Similarity	NPC477411
0.8058	Intermediate Similarity	NPC220893
0.8058	Intermediate Similarity	NPC173443
0.8049	Intermediate Similarity	NPC51292
0.8017	Intermediate Similarity	NPC228936
0.8016	Intermediate Similarity	NPC472394
0.8	Intermediate Similarity	NPC147561
0.8	Intermediate Similarity	NPC272946
0.8	Intermediate Similarity	NPC42234
0.7982	Intermediate Similarity	NPC473325
0.7967	Intermediate Similarity	NPC470765
0.7949	Intermediate Similarity	NPC135730
0.7949	Intermediate Similarity	NPC100353
0.7949	Intermediate Similarity	NPC226093
0.7937	Intermediate Similarity	NPC470278
0.7913	Intermediate Similarity	NPC212415
0.7909	Intermediate Similarity	NPC304873
0.7909	Intermediate Similarity	NPC284477
0.7903	Intermediate Similarity	NPC470753
0.7903	Intermediate Similarity	NPC473220
0.7899	Intermediate Similarity	NPC254233
0.7891	Intermediate Similarity	NPC329913
0.7876	Intermediate Similarity	NPC470391
0.7874	Intermediate Similarity	NPC238370
0.7874	Intermediate Similarity	NPC477360
0.787	Intermediate Similarity	NPC270654
0.7869	Intermediate Similarity	NPC472703
0.7869	Intermediate Similarity	NPC223351
0.7864	Intermediate Similarity	NPC89377
0.7857	Intermediate Similarity	NPC475508
0.7851	Intermediate Similarity	NPC144547
0.7845	Intermediate Similarity	NPC13784
0.7845	Intermediate Similarity	NPC474176
0.7838	Intermediate Similarity	NPC255676
0.7833	Intermediate Similarity	NPC202015
0.7829	Intermediate Similarity	NPC477896
0.7829	Intermediate Similarity	NPC477893
0.7826	Intermediate Similarity	NPC243355
0.7815	Intermediate Similarity	NPC45794
0.7815	Intermediate Similarity	NPC469574
0.7815	Intermediate Similarity	NPC228318
0.7812	Intermediate Similarity	NPC477364
0.7805	Intermediate Similarity	NPC471466
0.7805	Intermediate Similarity	NPC472704
0.7805	Intermediate Similarity	NPC51079
0.7795	Intermediate Similarity	NPC475478
0.7769	Intermediate Similarity	NPC238861
0.7769	Intermediate Similarity	NPC77000
0.7769	Intermediate Similarity	NPC289432
0.7769	Intermediate Similarity	NPC988
0.7768	Intermediate Similarity	NPC329282
0.7767	Intermediate Similarity	NPC318107
0.7759	Intermediate Similarity	NPC66208
0.7759	Intermediate Similarity	NPC158282
0.7759	Intermediate Similarity	NPC474314
0.7757	Intermediate Similarity	NPC261181
0.7752	Intermediate Similarity	NPC472591
0.7752	Intermediate Similarity	NPC477368
0.7752	Intermediate Similarity	NPC48929
0.7752	Intermediate Similarity	NPC477359
0.7752	Intermediate Similarity	NPC126516
0.7752	Intermediate Similarity	NPC474608
0.7752	Intermediate Similarity	NPC203486
0.7736	Intermediate Similarity	NPC119631
0.7734	Intermediate Similarity	NPC233860
0.7734	Intermediate Similarity	NPC233692
0.7734	Intermediate Similarity	NPC475569
0.7734	Intermediate Similarity	NPC239358
0.7727	Intermediate Similarity	NPC217621
0.7717	Intermediate Similarity	NPC471832
0.7717	Intermediate Similarity	NPC473247
0.7692	Intermediate Similarity	NPC472577
0.7692	Intermediate Similarity	NPC17877
0.7692	Intermediate Similarity	NPC291638
0.7692	Intermediate Similarity	NPC232888
0.7692	Intermediate Similarity	NPC475262
0.7692	Intermediate Similarity	NPC290833
0.7692	Intermediate Similarity	NPC195647
0.7692	Intermediate Similarity	NPC265459
0.7692	Intermediate Similarity	NPC311339
0.7692	Intermediate Similarity	NPC66761
0.7692	Intermediate Similarity	NPC270364
0.7692	Intermediate Similarity	NPC477367
0.7692	Intermediate Similarity	NPC473216
0.7692	Intermediate Similarity	NPC473399
0.768	Intermediate Similarity	NPC100402
0.768	Intermediate Similarity	NPC9180
0.7674	Intermediate Similarity	NPC472248
0.7674	Intermediate Similarity	NPC472656
0.767	Intermediate Similarity	NPC294134
0.767	Intermediate Similarity	NPC58616
0.7667	Intermediate Similarity	NPC152812
0.7661	Intermediate Similarity	NPC228739
0.7661	Intermediate Similarity	NPC328107
0.7661	Intermediate Similarity	NPC318067
0.7656	Intermediate Similarity	NPC469519
0.7652	Intermediate Similarity	NPC472395
0.7652	Intermediate Similarity	NPC472371
0.7642	Intermediate Similarity	NPC240108
0.7642	Intermediate Similarity	NPC213156
0.7634	Intermediate Similarity	NPC285221
0.7634	Intermediate Similarity	NPC477358
0.7634	Intermediate Similarity	NPC472374
0.7634	Intermediate Similarity	NPC194769
0.7634	Intermediate Similarity	NPC472372
0.7623	Intermediate Similarity	NPC232958
0.7619	Intermediate Similarity	NPC304760
0.7619	Intermediate Similarity	NPC472706
0.7619	Intermediate Similarity	NPC204579
0.7615	Intermediate Similarity	NPC136608
0.7615	Intermediate Similarity	NPC472250
0.7615	Intermediate Similarity	NPC38420
0.7615	Intermediate Similarity	NPC311492
0.7615	Intermediate Similarity	NPC153617
0.7615	Intermediate Similarity	NPC324898
0.7615	Intermediate Similarity	NPC134937
0.7615	Intermediate Similarity	NPC298547
0.7615	Intermediate Similarity	NPC28836
0.7611	Intermediate Similarity	NPC85977
0.7603	Intermediate Similarity	NPC293424
0.76	Intermediate Similarity	NPC470163
0.76	Intermediate Similarity	NPC470162

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC270699 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	856
0.2-0.3	1307
0.3-0.4	2701
0.4-0.5	2409
0.5-0.6	1222
0.6-0.7	374
0.7-0.8	50
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9709	High Similarity	NPD2182	Approved
0.932	High Similarity	NPD164	Approved
0.9159	High Similarity	NPD2181	Clinical (unspecified phase)
0.8396	Intermediate Similarity	NPD1238	Approved
0.7965	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2067	Discontinued
0.7769	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD9259	Approved
0.7767	Intermediate Similarity	NPD9257	Approved
0.7757	Intermediate Similarity	NPD1202	Approved
0.7717	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6287	Discontinued
0.7642	Intermediate Similarity	NPD3673	Approved
0.7642	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD3672	Approved
0.7615	Intermediate Similarity	NPD1989	Approved
0.7563	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5951	Approved
0.7524	Intermediate Similarity	NPD1087	Approved
0.7522	Intermediate Similarity	NPD6647	Phase 2
0.7477	Intermediate Similarity	NPD9258	Approved
0.7477	Intermediate Similarity	NPD9256	Approved
0.7456	Intermediate Similarity	NPD5909	Discontinued
0.7442	Intermediate Similarity	NPD7008	Discontinued
0.7411	Intermediate Similarity	NPD2066	Phase 3
0.7368	Intermediate Similarity	NPD1929	Approved
0.7368	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1930	Approved
0.7364	Intermediate Similarity	NPD6832	Phase 2
0.7344	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7631	Approved
0.7323	Intermediate Similarity	NPD1876	Approved
0.7317	Intermediate Similarity	NPD9545	Approved
0.7315	Intermediate Similarity	NPD1086	Approved
0.7315	Intermediate Similarity	NPD1090	Approved
0.7315	Intermediate Similarity	NPD1089	Approved
0.7302	Intermediate Similarity	NPD6637	Approved
0.7273	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD3764	Approved
0.7248	Intermediate Similarity	NPD7609	Phase 3
0.7222	Intermediate Similarity	NPD800	Approved
0.7207	Intermediate Similarity	NPD9260	Approved
0.7206	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7236	Approved
0.7188	Intermediate Similarity	NPD2198	Approved
0.7188	Intermediate Similarity	NPD2199	Approved
0.7182	Intermediate Similarity	NPD1088	Approved
0.7179	Intermediate Similarity	NPD3134	Approved
0.7168	Intermediate Similarity	NPD5926	Approved
0.7155	Intermediate Similarity	NPD1237	Approved
0.7154	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2629	Approved
0.713	Intermediate Similarity	NPD1932	Approved
0.7111	Intermediate Similarity	NPD2567	Approved
0.7111	Intermediate Similarity	NPD2569	Approved
0.7087	Intermediate Similarity	NPD9490	Approved
0.7083	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2346	Discontinued
0.708	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1019	Discontinued
0.7077	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6085	Phase 2
0.7064	Intermediate Similarity	NPD5347	Phase 2
0.7064	Intermediate Similarity	NPD5346	Phase 2
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD2329	Discontinued
0.7054	Intermediate Similarity	NPD1693	Approved
0.7049	Intermediate Similarity	NPD1241	Discontinued
0.7045	Intermediate Similarity	NPD6039	Approved
0.7031	Intermediate Similarity	NPD3972	Approved
0.7018	Intermediate Similarity	NPD9495	Approved
0.7015	Intermediate Similarity	NPD3373	Approved
0.7	Intermediate Similarity	NPD5236	Approved
0.7	Intermediate Similarity	NPD1317	Discontinued
0.7	Intermediate Similarity	NPD5235	Approved
0.7	Intermediate Similarity	NPD5237	Approved
0.7	Intermediate Similarity	NPD5239	Approved
0.7	Intermediate Similarity	NPD5240	Approved
0.6992	Remote Similarity	NPD2313	Discontinued
0.6984	Remote Similarity	NPD5691	Approved
0.6981	Remote Similarity	NPD9491	Approved
0.6975	Remote Similarity	NPD1358	Approved
0.6967	Remote Similarity	NPD7094	Approved
0.6967	Remote Similarity	NPD6858	Approved
0.6967	Remote Similarity	NPD5277	Phase 2
0.6964	Remote Similarity	NPD1563	Approved
0.696	Remote Similarity	NPD2347	Approved
0.6953	Remote Similarity	NPD1281	Approved
0.6953	Remote Similarity	NPD4807	Approved
0.6953	Remote Similarity	NPD4806	Approved
0.6947	Remote Similarity	NPD2798	Approved
0.6944	Remote Similarity	NPD7239	Suspended
0.6942	Remote Similarity	NPD2201	Approved
0.694	Remote Similarity	NPD7713	Phase 3
0.694	Remote Similarity	NPD7961	Discontinued
0.6935	Remote Similarity	NPD4198	Discontinued
0.6929	Remote Similarity	NPD5305	Approved
0.6929	Remote Similarity	NPD5306	Approved
0.6923	Remote Similarity	NPD5667	Approved
0.6923	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD9717	Approved
0.6891	Remote Similarity	NPD6685	Approved
0.6889	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD650	Approved
0.6881	Remote Similarity	NPD4793	Discontinued
0.687	Remote Similarity	NPD553	Approved
0.687	Remote Similarity	NPD3267	Approved
0.687	Remote Similarity	NPD3266	Approved
0.687	Remote Similarity	NPD552	Approved
0.687	Remote Similarity	NPD9567	Approved
0.687	Remote Similarity	NPD2797	Approved
0.686	Remote Similarity	NPD4234	Approved
0.686	Remote Similarity	NPD4233	Approved
0.6855	Remote Similarity	NPD4766	Approved
0.685	Remote Similarity	NPD5585	Approved
0.6846	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4622	Approved
0.6838	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4618	Approved
0.6827	Remote Similarity	NPD225	Approved
0.6827	Remote Similarity	NPD227	Approved
0.6825	Remote Similarity	NPD6065	Approved
0.6822	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3748	Approved
0.681	Remote Similarity	NPD7798	Approved
0.6809	Remote Similarity	NPD4628	Phase 3
0.6809	Remote Similarity	NPD7003	Approved
0.6806	Remote Similarity	NPD6273	Approved
0.6797	Remote Similarity	NPD17	Approved
0.6794	Remote Similarity	NPD1283	Approved
0.6788	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1239	Approved
0.6783	Remote Similarity	NPD3495	Discontinued
0.6783	Remote Similarity	NPD1565	Approved
0.6783	Remote Similarity	NPD1566	Phase 3
0.6783	Remote Similarity	NPD1564	Approved
0.6781	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.678	Remote Similarity	NPD9261	Approved
0.6774	Remote Similarity	NPD2652	Approved
0.6774	Remote Similarity	NPD2650	Approved
0.6769	Remote Similarity	NPD4878	Approved
0.6765	Remote Similarity	NPD4307	Phase 2
0.6763	Remote Similarity	NPD2531	Phase 2
0.6763	Remote Similarity	NPD2935	Discontinued
0.6763	Remote Similarity	NPD2438	Suspended
0.6744	Remote Similarity	NPD4136	Approved
0.6744	Remote Similarity	NPD4135	Approved
0.6744	Remote Similarity	NPD4106	Approved
0.6741	Remote Similarity	NPD3268	Approved
0.6739	Remote Similarity	NPD2670	Approved
0.6739	Remote Similarity	NPD5689	Approved
0.6739	Remote Similarity	NPD5688	Approved
0.6738	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1282	Approved
0.6726	Remote Similarity	NPD1508	Approved
0.6723	Remote Similarity	NPD3048	Approved
0.6723	Remote Similarity	NPD3047	Approved
0.6723	Remote Similarity	NPD3046	Approved
0.6721	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1756	Approved
0.6721	Remote Similarity	NPD1752	Approved
0.6715	Remote Similarity	NPD230	Phase 1
0.6715	Remote Similarity	NPD6355	Discontinued
0.6714	Remote Similarity	NPD7611	Approved
0.6694	Remote Similarity	NPD2607	Approved
0.6691	Remote Similarity	NPD8032	Phase 2
0.669	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3971	Phase 1
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3887	Approved
0.6641	Remote Similarity	NPD1608	Approved
0.6641	Remote Similarity	NPD1894	Discontinued
0.6639	Remote Similarity	NPD5765	Approved
0.6636	Remote Similarity	NPD226	Approved
0.6621	Remote Similarity	NPD2532	Approved
0.6621	Remote Similarity	NPD2534	Approved
0.6621	Remote Similarity	NPD2533	Approved
0.6617	Remote Similarity	NPD6362	Approved
0.6617	Remote Similarity	NPD1203	Approved
0.6615	Remote Similarity	NPD3496	Discontinued
0.6614	Remote Similarity	NPD4574	Approved
0.6614	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4576	Approved
0.6613	Remote Similarity	NPD9508	Approved
0.6613	Remote Similarity	NPD969	Suspended
0.66	Remote Similarity	NPD7819	Suspended
0.6597	Remote Similarity	NPD7440	Discontinued
0.6596	Remote Similarity	NPD1471	Phase 3
0.6594	Remote Similarity	NPD1933	Approved
0.6594	Remote Similarity	NPD447	Suspended
0.6591	Remote Similarity	NPD4359	Approved
0.6589	Remote Similarity	NPD4102	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data