NPASS Compound

Structure

CID162205 OpenBabel06191715532D 26 27 0 0 1 0 0 0 0 0999 V2000 2.6396 -5.6352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2238 -3.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6886 -5.3261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8710 -1.0354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 -3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 11 2 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 15 16 1 0 0 0 0 15 25 1 6 0 0 0 16 13 1 1 0 0 0 16 18 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 1 0 0 0 18 26 1 6 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	371.649
LogP:	1.774
LogD:	1.112
LogS:	-3.275
# Rotatable Bonds:	3
TPSA:	86.74
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.556
Synthetic Accessibility Score:	4.951
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.635
MDCK Permeability:	1.6611009414191358e-05
Pgp-inhibitor:	0.904
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.749

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	89.14946746826172%
Volume Distribution (VD):	0.602
Pgp-substrate:	7.09368371963501%

ADMET: Metabolism

CYP1A2-inhibitor:	0.886
CYP1A2-substrate:	0.692
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.131
CYP2C9-inhibitor:	0.946
CYP2C9-substrate:	0.207
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	5.174
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.355
Drug-inuced Liver Injury (DILI):	0.82
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.923
Carcinogencity:	0.163
Eye Corrosion:	0.015
Eye Irritation:	0.124
Respiratory Toxicity:	0.828

Download Data

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

Natural Product: NPC162205

Natural Product ID:	NPC162205
*Common Name:**	Molephantinin
IUPAC Name:	[(3aR,4S,6E,9Z,11S,11aS)-11-hydroxy-6,10-dimethyl-3-methylidene-2,8-dioxo-4,5,11,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] (E)-2-methylbut-2-enoate
Synonyms:	Molephantinin
Standard InCHIKey:	VUURQISRHJCAJY-CXRMMEALSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-6-11(3)19(23)25-15-8-10(2)7-14(21)9-12(4)17(22)18-16(15)13(5)20(24)26-18/h6-7,9,15-18,22H,5,8H2,1-4H3/b10-7+,11-6+,12-9-/t15-,16+,17-,18-/m0/s1
SMILES:	C/C=C(/C(=O)O[C@H]1C/C(=C/C(=O)/C=C([C@@H]([C@@H]2[C@@H]1C(=C)C(=O)O2)O)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL189129
PubChem CID:	5281485
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075766]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[18239317]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[18239317]
NPO3141	Saracha punctata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834160]
NPO7088	Staphylea bumalda	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7088	Staphylea bumalda	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7088	Staphylea bumalda	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7278	Astragalus caprinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5586	Kickxia elatine	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12443	Torrubiella hemipterigena	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4881	Senecio kilimanjari	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4076	Lubomirskia baicalensis	Species	Lubomirskiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8580	Caloplaca ferruginea	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5991	Arcopilus aureus	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5318	Rotheca serrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3141	Saracha punctata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5195	Odontites vernus	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO343	Cryptosphaeria eunomia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4618	Ilex oldhami	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO171	Relbunium hypocarpium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3657	Hyalis argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5789	Ocotea acutangula	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8855	Fromia milleporella	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4439	Epaltes mexicana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24759	Schotia brachypetala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7088	Staphylea bumalda	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6503	Marsdenia rostrata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7641	Petunia hybr	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3325	Cineraria parvifolia	Species	Asteraceae	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
Others	4

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	10.0	uM	PMID[511914]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-1.0	n.a.	PMID[511914]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	10.0	uM	PMID[511915]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	397.0	%	PMID[511916]

☑ 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 NPC162205 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	197
0.1-0.2	1195
0.2-0.3	4665
0.3-0.4	8466
0.4-0.5	15220
0.5-0.6	7449
0.6-0.7	4051
0.7-0.8	1122
0.8-0.85	212
0.85-0.9	102
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC295204
1.0	High Similarity	NPC288240
1.0	High Similarity	NPC273579
0.9655	High Similarity	NPC473321
0.954	High Similarity	NPC473619
0.931	High Similarity	NPC473715
0.9231	High Similarity	NPC477921
0.9205	High Similarity	NPC474032
0.9186	High Similarity	NPC21469
0.9121	High Similarity	NPC471142
0.9121	High Similarity	NPC477922
0.9111	High Similarity	NPC475912
0.9011	High Similarity	NPC303942
0.9011	High Similarity	NPC57405
0.8953	High Similarity	NPC40746
0.8953	High Similarity	NPC169575
0.8936	High Similarity	NPC288876
0.8913	High Similarity	NPC14961
0.8913	High Similarity	NPC270013
0.8913	High Similarity	NPC36954
0.8889	High Similarity	NPC474232
0.8864	High Similarity	NPC475461
0.8864	High Similarity	NPC469910
0.8864	High Similarity	NPC305475
0.8851	High Similarity	NPC141193
0.8851	High Similarity	NPC96259
0.883	High Similarity	NPC471144
0.883	High Similarity	NPC473326
0.8817	High Similarity	NPC473859
0.8817	High Similarity	NPC279621
0.8804	High Similarity	NPC474035
0.8804	High Similarity	NPC81386
0.8791	High Similarity	NPC184463
0.8791	High Similarity	NPC30515
0.875	High Similarity	NPC470755
0.875	High Similarity	NPC149371
0.875	High Similarity	NPC255307
0.8736	High Similarity	NPC116543
0.8736	High Similarity	NPC473390
0.8736	High Similarity	NPC131669
0.8721	High Similarity	NPC24417
0.871	High Similarity	NPC475659
0.8696	High Similarity	NPC81419
0.8696	High Similarity	NPC179746
0.8696	High Similarity	NPC212486
0.8696	High Similarity	NPC476300
0.8696	High Similarity	NPC125674
0.8696	High Similarity	NPC228451
0.8696	High Similarity	NPC475838
0.8681	High Similarity	NPC474761
0.8681	High Similarity	NPC51004
0.8681	High Similarity	NPC144133
0.8681	High Similarity	NPC179394
0.8681	High Similarity	NPC476004
0.8681	High Similarity	NPC475855
0.8667	High Similarity	NPC202672
0.8667	High Similarity	NPC476803
0.8667	High Similarity	NPC475819
0.8652	High Similarity	NPC112685
0.8646	High Similarity	NPC47880
0.8636	High Similarity	NPC191476
0.8636	High Similarity	NPC114979
0.8636	High Similarity	NPC476804
0.8636	High Similarity	NPC158756
0.8632	High Similarity	NPC474213
0.8621	High Similarity	NPC229825
0.8617	High Similarity	NPC476315
0.8602	High Similarity	NPC474247
0.8587	High Similarity	NPC12172
0.8587	High Similarity	NPC208886
0.8571	High Similarity	NPC295312
0.8571	High Similarity	NPC280612
0.8571	High Similarity	NPC307411
0.8571	High Similarity	NPC100487
0.8542	High Similarity	NPC475949
0.8523	High Similarity	NPC59097
0.8511	High Similarity	NPC471141
0.8495	Intermediate Similarity	NPC469645
0.8495	Intermediate Similarity	NPC11456
0.8495	Intermediate Similarity	NPC469692
0.8488	Intermediate Similarity	NPC167881
0.8488	Intermediate Similarity	NPC270126
0.8488	Intermediate Similarity	NPC98557
0.8469	Intermediate Similarity	NPC475871
0.8469	Intermediate Similarity	NPC472755
0.8469	Intermediate Similarity	NPC475945
0.8462	Intermediate Similarity	NPC476805
0.8454	Intermediate Similarity	NPC133907
0.8454	Intermediate Similarity	NPC476270
0.8454	Intermediate Similarity	NPC185141
0.8454	Intermediate Similarity	NPC164598
0.8454	Intermediate Similarity	NPC110443
0.8454	Intermediate Similarity	NPC474339
0.8454	Intermediate Similarity	NPC46998
0.8454	Intermediate Similarity	NPC128733
0.8444	Intermediate Similarity	NPC308412
0.8444	Intermediate Similarity	NPC134885
0.8444	Intermediate Similarity	NPC134807
0.8444	Intermediate Similarity	NPC210218
0.8444	Intermediate Similarity	NPC204686
0.8444	Intermediate Similarity	NPC219498
0.8444	Intermediate Similarity	NPC473687
0.8444	Intermediate Similarity	NPC150755
0.8438	Intermediate Similarity	NPC187268
0.8421	Intermediate Similarity	NPC230800
0.8421	Intermediate Similarity	NPC306041
0.8404	Intermediate Similarity	NPC473316
0.8404	Intermediate Similarity	NPC121825
0.8404	Intermediate Similarity	NPC473330
0.84	Intermediate Similarity	NPC477513
0.8384	Intermediate Similarity	NPC203659
0.8372	Intermediate Similarity	NPC108816
0.8372	Intermediate Similarity	NPC196653
0.8372	Intermediate Similarity	NPC471465
0.8372	Intermediate Similarity	NPC93763
0.837	Intermediate Similarity	NPC477011
0.837	Intermediate Similarity	NPC166919
0.837	Intermediate Similarity	NPC477016
0.837	Intermediate Similarity	NPC477017
0.837	Intermediate Similarity	NPC151770
0.8367	Intermediate Similarity	NPC324017
0.8367	Intermediate Similarity	NPC320019
0.8367	Intermediate Similarity	NPC474747
0.8352	Intermediate Similarity	NPC178215
0.8352	Intermediate Similarity	NPC179659
0.8333	Intermediate Similarity	NPC132496
0.8333	Intermediate Similarity	NPC286338
0.8333	Intermediate Similarity	NPC231009
0.8333	Intermediate Similarity	NPC110710
0.8333	Intermediate Similarity	NPC473651
0.8333	Intermediate Similarity	NPC283085
0.8333	Intermediate Similarity	NPC473478
0.8333	Intermediate Similarity	NPC473669
0.8333	Intermediate Similarity	NPC103284
0.8333	Intermediate Similarity	NPC165162
0.8333	Intermediate Similarity	NPC223871
0.8333	Intermediate Similarity	NPC82795
0.8333	Intermediate Similarity	NPC66346
0.8333	Intermediate Similarity	NPC1083
0.8333	Intermediate Similarity	NPC107986
0.83	Intermediate Similarity	NPC243998
0.8298	Intermediate Similarity	NPC475302
0.8295	Intermediate Similarity	NPC52861
0.8283	Intermediate Similarity	NPC110989
0.828	Intermediate Similarity	NPC251385
0.828	Intermediate Similarity	NPC106510
0.828	Intermediate Similarity	NPC473448
0.828	Intermediate Similarity	NPC71533
0.828	Intermediate Similarity	NPC469368
0.828	Intermediate Similarity	NPC49342
0.828	Intermediate Similarity	NPC129419
0.8265	Intermediate Similarity	NPC201718
0.8265	Intermediate Similarity	NPC15993
0.8265	Intermediate Similarity	NPC474742
0.8265	Intermediate Similarity	NPC472753
0.8261	Intermediate Similarity	NPC21208
0.8261	Intermediate Similarity	NPC280621
0.8261	Intermediate Similarity	NPC20339
0.8261	Intermediate Similarity	NPC48338
0.8261	Intermediate Similarity	NPC89001
0.8261	Intermediate Similarity	NPC153805
0.8261	Intermediate Similarity	NPC40376
0.8261	Intermediate Similarity	NPC233551
0.8256	Intermediate Similarity	NPC141789
0.8256	Intermediate Similarity	NPC171204
0.8256	Intermediate Similarity	NPC320630
0.8256	Intermediate Similarity	NPC116177
0.8256	Intermediate Similarity	NPC7563
0.8256	Intermediate Similarity	NPC476028
0.8242	Intermediate Similarity	NPC279267
0.8242	Intermediate Similarity	NPC103523
0.8242	Intermediate Similarity	NPC475581
0.8242	Intermediate Similarity	NPC62118
0.8242	Intermediate Similarity	NPC171174
0.8242	Intermediate Similarity	NPC69082
0.8242	Intermediate Similarity	NPC142117
0.8242	Intermediate Similarity	NPC114694
0.8242	Intermediate Similarity	NPC232555
0.8242	Intermediate Similarity	NPC134865
0.8242	Intermediate Similarity	NPC107717
0.8242	Intermediate Similarity	NPC240695
0.8242	Intermediate Similarity	NPC477015
0.8242	Intermediate Similarity	NPC477010
0.8242	Intermediate Similarity	NPC231096
0.8222	Intermediate Similarity	NPC243618
0.8222	Intermediate Similarity	NPC163093
0.8222	Intermediate Similarity	NPC70424
0.8211	Intermediate Similarity	NPC71589
0.8211	Intermediate Similarity	NPC471147
0.8211	Intermediate Similarity	NPC190294
0.82	Intermediate Similarity	NPC474741
0.8182	Intermediate Similarity	NPC470947
0.8182	Intermediate Similarity	NPC281132
0.8182	Intermediate Similarity	NPC86077
0.8182	Intermediate Similarity	NPC470945
0.8182	Intermediate Similarity	NPC471148
0.8182	Intermediate Similarity	NPC470946
0.8182	Intermediate Similarity	NPC472754
0.8182	Intermediate Similarity	NPC225353
0.8172	Intermediate Similarity	NPC14901

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 NPC162205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1800
0.2-0.3	3671
0.3-0.4	2284
0.4-0.5	800
0.5-0.6	301
0.6-0.7	86
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD6698	Approved
0.8085	Intermediate Similarity	NPD46	Approved
0.7812	Intermediate Similarity	NPD7983	Approved
0.7755	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6371	Approved
0.7526	Intermediate Similarity	NPD7838	Discovery
0.7524	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4225	Approved
0.7347	Intermediate Similarity	NPD5785	Approved
0.7188	Intermediate Similarity	NPD5363	Approved
0.7184	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7154	Phase 3
0.713	Intermediate Similarity	NPD6686	Approved
0.7113	Intermediate Similarity	NPD5786	Approved
0.7113	Intermediate Similarity	NPD4249	Approved
0.7091	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6435	Approved
0.7041	Intermediate Similarity	NPD4250	Approved
0.7041	Intermediate Similarity	NPD4251	Approved
0.703	Intermediate Similarity	NPD5779	Approved
0.703	Intermediate Similarity	NPD5778	Approved
0.7021	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.69	Remote Similarity	NPD1695	Approved
0.6887	Remote Similarity	NPD5344	Discontinued
0.6875	Remote Similarity	NPD4270	Approved
0.6875	Remote Similarity	NPD4269	Approved
0.6842	Remote Similarity	NPD5368	Approved
0.6842	Remote Similarity	NPD4252	Approved
0.6838	Remote Similarity	NPD8517	Approved
0.6838	Remote Similarity	NPD8515	Approved
0.6838	Remote Similarity	NPD8516	Approved
0.6838	Remote Similarity	NPD8513	Phase 3
0.6827	Remote Similarity	NPD7839	Suspended
0.6809	Remote Similarity	NPD4268	Approved
0.6809	Remote Similarity	NPD4271	Approved
0.6804	Remote Similarity	NPD5362	Discontinued
0.6804	Remote Similarity	NPD6110	Phase 1
0.6783	Remote Similarity	NPD7115	Discovery
0.6726	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6635	Remote Similarity	NPD5282	Discontinued
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5369	Approved
0.6583	Remote Similarity	NPD7642	Approved
0.6581	Remote Similarity	NPD7641	Discontinued
0.6557	Remote Similarity	NPD8074	Phase 3
0.6531	Remote Similarity	NPD5209	Approved
0.6531	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4756	Discovery
0.6481	Remote Similarity	NPD6648	Approved
0.6481	Remote Similarity	NPD7639	Approved
0.6481	Remote Similarity	NPD7640	Approved
0.646	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7829	Approved
0.6446	Remote Similarity	NPD7830	Approved
0.6444	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6101	Approved
0.6408	Remote Similarity	NPD5370	Suspended
0.6408	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7638	Approved
0.6379	Remote Similarity	NPD4632	Approved
0.6341	Remote Similarity	NPD7507	Approved
0.6333	Remote Similarity	NPD6319	Approved
0.63	Remote Similarity	NPD5331	Approved
0.63	Remote Similarity	NPD5332	Approved
0.6293	Remote Similarity	NPD8297	Approved
0.6286	Remote Similarity	NPD6411	Approved
0.6286	Remote Similarity	NPD7637	Suspended
0.6286	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6412	Phase 2
0.6283	Remote Similarity	NPD5697	Approved
0.6281	Remote Similarity	NPD8444	Approved
0.6263	Remote Similarity	NPD4790	Discontinued
0.6261	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6881	Approved
0.6228	Remote Similarity	NPD6899	Approved
0.6228	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6399	Phase 3
0.6222	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7260	Phase 2
0.6207	Remote Similarity	NPD6649	Approved
0.6207	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6650	Approved
0.6195	Remote Similarity	NPD6675	Approved
0.6195	Remote Similarity	NPD7128	Approved
0.6195	Remote Similarity	NPD6008	Approved
0.6195	Remote Similarity	NPD5739	Approved
0.6195	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD7319	Approved
0.6174	Remote Similarity	NPD6013	Approved
0.6174	Remote Similarity	NPD6012	Approved
0.6174	Remote Similarity	NPD6014	Approved
0.6174	Remote Similarity	NPD6373	Approved
0.6174	Remote Similarity	NPD6372	Approved
0.6154	Remote Similarity	NPD7331	Phase 2
0.614	Remote Similarity	NPD5701	Approved
0.6129	Remote Similarity	NPD7492	Approved
0.6121	Remote Similarity	NPD6883	Approved
0.6121	Remote Similarity	NPD7102	Approved
0.6121	Remote Similarity	NPD6421	Discontinued
0.6121	Remote Similarity	NPD7290	Approved
0.6117	Remote Similarity	NPD6422	Discontinued
0.6111	Remote Similarity	NPD3197	Phase 1
0.6087	Remote Similarity	NPD6011	Approved
0.6087	Remote Similarity	NPD7320	Approved
0.6083	Remote Similarity	NPD7500	Approved
0.6083	Remote Similarity	NPD6009	Approved
0.608	Remote Similarity	NPD6616	Approved
0.608	Remote Similarity	NPD8451	Approved
0.6071	Remote Similarity	NPD5211	Phase 2
0.6068	Remote Similarity	NPD6869	Approved
0.6068	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6847	Approved
0.6068	Remote Similarity	NPD2204	Approved
0.6068	Remote Similarity	NPD6617	Approved
0.6066	Remote Similarity	NPD6054	Approved
0.6055	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8328	Phase 3
0.6047	Remote Similarity	NPD6845	Suspended
0.604	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7078	Approved
0.6032	Remote Similarity	NPD8448	Approved
0.6018	Remote Similarity	NPD6647	Phase 2
0.6017	Remote Similarity	NPD6882	Approved
0.6016	Remote Similarity	NPD6015	Approved
0.6016	Remote Similarity	NPD6016	Approved
0.6016	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.5984	Remote Similarity	NPD7736	Approved
0.5983	Remote Similarity	NPD4634	Approved
0.5979	Remote Similarity	NPD8039	Approved
0.5968	Remote Similarity	NPD5988	Approved
0.5968	Remote Similarity	NPD6370	Approved
0.5965	Remote Similarity	NPD5141	Approved
0.5963	Remote Similarity	NPD5695	Phase 3
0.5952	Remote Similarity	NPD8273	Phase 1
0.5946	Remote Similarity	NPD5696	Approved
0.5935	Remote Similarity	NPD6059	Approved
0.5929	Remote Similarity	NPD7632	Discontinued
0.592	Remote Similarity	NPD7604	Phase 2
0.5906	Remote Similarity	NPD8293	Discontinued
0.5905	Remote Similarity	NPD7524	Approved
0.5893	Remote Similarity	NPD4696	Approved
0.5893	Remote Similarity	NPD5285	Approved
0.5893	Remote Similarity	NPD5286	Approved
0.5891	Remote Similarity	NPD8392	Approved
0.5891	Remote Similarity	NPD8390	Approved
0.5891	Remote Similarity	NPD8391	Approved
0.5872	Remote Similarity	NPD7748	Approved
0.587	Remote Similarity	NPD7341	Phase 2
0.5868	Remote Similarity	NPD6274	Approved
0.5856	Remote Similarity	NPD4755	Approved
0.5847	Remote Similarity	NPD2067	Discontinued
0.584	Remote Similarity	NPD8080	Discontinued
0.5833	Remote Similarity	NPD7515	Phase 2
0.5833	Remote Similarity	NPD6079	Approved
0.5827	Remote Similarity	NPD6336	Discontinued
0.5824	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7505	Discontinued
0.581	Remote Similarity	NPD7521	Approved
0.581	Remote Similarity	NPD5330	Approved
0.581	Remote Similarity	NPD6684	Approved
0.581	Remote Similarity	NPD7146	Approved
0.581	Remote Similarity	NPD6409	Approved
0.581	Remote Similarity	NPD7334	Approved
0.581	Remote Similarity	NPD3618	Phase 1
0.5806	Remote Similarity	NPD3704	Approved
0.5798	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5328	Approved
0.5789	Remote Similarity	NPD5224	Approved
0.5789	Remote Similarity	NPD4633	Approved
0.5789	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5225	Approved
0.5789	Remote Similarity	NPD5226	Approved
0.5778	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7328	Approved
0.5772	Remote Similarity	NPD7327	Approved
0.5769	Remote Similarity	NPD3133	Approved
0.5769	Remote Similarity	NPD3666	Approved
0.5769	Remote Similarity	NPD3665	Phase 1
0.5769	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4697	Phase 3
0.5766	Remote Similarity	NPD5221	Approved
0.5766	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5222	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