NPASS Compound

Structure

CID312833 OpenBabel06191716122D 36 40 0 0 1 0 0 0 0 0999 V2000 3.9170 -4.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0543 -3.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4128 -3.6190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7379 -0.5244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3387 -2.7608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1408 -2.6301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3760 -1.1599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3114 -0.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1033 -3.4174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3977 -2.6113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7638 -2.2578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0099 -1.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4931 -2.2766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5250 -1.7703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0207 -2.2390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2165 -0.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8094 -1.4476 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1191 -1.1787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3193 -0.9585 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2850 0.0651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7326 -2.1356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8608 0.5370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7530 -1.5321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5039 -1.5510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0079 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8751 -0.9964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4759 -1.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9010 -2.7298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1751 -0.1481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0691 1.0087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5866 -2.6709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7523 0.0668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8222 1.5441 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 1.1468 -2.5046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7603 -1.1137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 11 1 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 23 1 0 0 0 0 8 34 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 23 1 1 0 0 0 12 15 1 0 0 0 0 12 26 2 0 0 0 0 13 24 1 6 0 0 0 13 35 1 0 0 0 0 14 27 2 0 0 0 0 14 36 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 16 29 1 1 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 17 36 1 1 0 0 0 18 23 1 1 0 0 0 18 24 1 0 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 20 25 1 6 0 0 0 20 30 1 0 0 0 0 21 31 2 0 0 0 0 21 35 1 0 0 0 0 22 32 2 0 0 0 0 22 33 1 0 0 0 0 23 4 1 1 0 0 0 24 8 1 1 0 0 0 25 22 1 6 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.18
Volume:	479.048
LogP:	0.935
LogD:	0.136
LogS:	-3.599
# Rotatable Bonds:	4
TPSA:	173.73
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	6.612
Fsp3:	0.72
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.606
MDCK Permeability:	9.657521150074899e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.842
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	46.88994598388672%
Volume Distribution (VD):	0.276
Pgp-substrate:	42.65338897705078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	2.182
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.278
Carcinogencity:	0.144
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC312833

Natural Product ID:	NPC312833
*Common Name:**	RIYGDELXURVOBZ-HVCNMUSHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RIYGDELXURVOBZ-HVCNMUSHSA-N
Standard InCHI:	InChI=1S/C25H30O11/c1-9(2)5-14(27)36-17-19-24-8-34-25(19,22(32)33)20(30)16(29)18(24)23(4)7-12(26)15(28)10(3)11(23)6-13(24)35-21(17)31/h5,11,13,16-20,28-30H,6-8H2,1-4H3,(H,32,33)/t11-,13+,16+,17+,18+,19+,20-,23-,24+,25+/m0/s1
SMILES:	CC(=CC(=O)O[C@H]1C(=O)O[C@H]2[C@]34[C@@H]1[C@](OC3)(C(=O)O)[C@@H](O)[C@@H]([C@@H]4[C@@]1([C@@H](C2)C(=C(C(=O)C1)O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342216
PubChem CID:	10391474
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15949825]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18723353]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26522747]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350091]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10818	Carpobrotus edulis	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14845	Ceratophyllum submersum	Species	Ceratophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9203	Cephalonomia gallicola	Species	Bethylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14749	Lippia carviodora	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5303	Castanea crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3164	Yponomeuta malinellus	Species	Yponomeutidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14528	Pneumatospora obcoronata	n.a.	n.a.	n.a.	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
IC50	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[508300]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[508300]

☑ 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 NPC312833 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	256
0.1-0.2	1498
0.2-0.3	4160
0.3-0.4	6877
0.4-0.5	10746
0.5-0.6	9382
0.6-0.7	5918
0.7-0.8	3281
0.8-0.85	420
0.85-0.9	75
0.9-0.95	64
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC91693
0.9912	High Similarity	NPC105926
0.9912	High Similarity	NPC18945
0.9912	High Similarity	NPC265557
0.9825	High Similarity	NPC24651
0.9825	High Similarity	NPC476729
0.9565	High Similarity	NPC67251
0.9561	High Similarity	NPC470779
0.9487	High Similarity	NPC476008
0.9469	High Similarity	NPC17772
0.9402	High Similarity	NPC477745
0.9386	High Similarity	NPC470777
0.9375	High Similarity	NPC323821
0.9375	High Similarity	NPC143268
0.9375	High Similarity	NPC268238
0.9375	High Similarity	NPC45218
0.9298	High Similarity	NPC470776
0.9292	High Similarity	NPC173686
0.9292	High Similarity	NPC16081
0.9211	High Similarity	NPC470854
0.9211	High Similarity	NPC473590
0.9211	High Similarity	NPC146432
0.9211	High Similarity	NPC470778
0.9211	High Similarity	NPC287343
0.9211	High Similarity	NPC97908
0.9211	High Similarity	NPC474654
0.9211	High Similarity	NPC122033
0.9204	High Similarity	NPC299849
0.9153	High Similarity	NPC470922
0.913	High Similarity	NPC251310
0.9123	High Similarity	NPC213084
0.9123	High Similarity	NPC190185
0.9123	High Similarity	NPC40632
0.9123	High Similarity	NPC328374
0.9123	High Similarity	NPC251236
0.9123	High Similarity	NPC89929
0.9123	High Similarity	NPC96312
0.9115	High Similarity	NPC49451
0.9115	High Similarity	NPC94509
0.9106	High Similarity	NPC262813
0.9043	High Similarity	NPC176513
0.9043	High Similarity	NPC470775
0.9035	High Similarity	NPC473798
0.9032	High Similarity	NPC190065
0.9032	High Similarity	NPC251998
0.9032	High Similarity	NPC471089
0.9032	High Similarity	NPC141215
0.8974	High Similarity	NPC112038
0.8974	High Similarity	NPC107338
0.8974	High Similarity	NPC109607
0.8966	High Similarity	NPC188667
0.8966	High Similarity	NPC297179
0.8966	High Similarity	NPC204552
0.896	High Similarity	NPC295885
0.896	High Similarity	NPC140045
0.896	High Similarity	NPC596
0.8957	High Similarity	NPC474734
0.8947	High Similarity	NPC7921
0.8947	High Similarity	NPC208998
0.8943	High Similarity	NPC168879
0.8898	High Similarity	NPC477046
0.8898	High Similarity	NPC102822
0.8889	High Similarity	NPC475775
0.8889	High Similarity	NPC476529
0.8793	High Similarity	NPC152199
0.8793	High Similarity	NPC235539
0.8793	High Similarity	NPC207217
0.8793	High Similarity	NPC134869
0.8772	High Similarity	NPC171888
0.8772	High Similarity	NPC146945
0.8729	High Similarity	NPC469488
0.871	High Similarity	NPC102316
0.8707	High Similarity	NPC18547
0.8707	High Similarity	NPC474906
0.8696	High Similarity	NPC11252
0.8696	High Similarity	NPC289312
0.8696	High Similarity	NPC474516
0.8689	High Similarity	NPC470780
0.8673	High Similarity	NPC293850
0.8632	High Similarity	NPC470628
0.8632	High Similarity	NPC474046
0.8632	High Similarity	NPC259306
0.8621	High Similarity	NPC51978
0.8621	High Similarity	NPC198539
0.8618	High Similarity	NPC475636
0.8618	High Similarity	NPC295220
0.8609	High Similarity	NPC201992
0.8607	High Similarity	NPC181999
0.8607	High Similarity	NPC87662
0.8584	High Similarity	NPC144854
0.8584	High Similarity	NPC3316
0.8583	High Similarity	NPC243014
0.856	High Similarity	NPC478154
0.8559	High Similarity	NPC473968
0.8559	High Similarity	NPC53396
0.8559	High Similarity	NPC58662
0.8559	High Similarity	NPC469684
0.8559	High Similarity	NPC98249
0.8548	High Similarity	NPC309096
0.8548	High Similarity	NPC476851
0.8548	High Similarity	NPC54614
0.8547	High Similarity	NPC469877
0.8547	High Similarity	NPC470919
0.8547	High Similarity	NPC117712
0.8534	High Similarity	NPC302146
0.8534	High Similarity	NPC269530
0.8534	High Similarity	NPC472002
0.8512	High Similarity	NPC269642
0.8509	High Similarity	NPC154608
0.8509	High Similarity	NPC277017
0.8509	High Similarity	NPC192813
0.85	High Similarity	NPC472004
0.85	High Similarity	NPC478051
0.8492	Intermediate Similarity	NPC478151
0.8487	Intermediate Similarity	NPC240509
0.8487	Intermediate Similarity	NPC284707
0.848	Intermediate Similarity	NPC262796
0.848	Intermediate Similarity	NPC45346
0.848	Intermediate Similarity	NPC134914
0.848	Intermediate Similarity	NPC478064
0.848	Intermediate Similarity	NPC329993
0.848	Intermediate Similarity	NPC478155
0.848	Intermediate Similarity	NPC264566
0.848	Intermediate Similarity	NPC476074
0.848	Intermediate Similarity	NPC173435
0.848	Intermediate Similarity	NPC301639
0.848	Intermediate Similarity	NPC478065
0.848	Intermediate Similarity	NPC476852
0.848	Intermediate Similarity	NPC475377
0.848	Intermediate Similarity	NPC25998
0.848	Intermediate Similarity	NPC172374
0.848	Intermediate Similarity	NPC475167
0.8475	Intermediate Similarity	NPC179626
0.8475	Intermediate Similarity	NPC270478
0.8468	Intermediate Similarity	NPC476859
0.8468	Intermediate Similarity	NPC188291
0.8462	Intermediate Similarity	NPC478212
0.8462	Intermediate Similarity	NPC477126
0.8455	Intermediate Similarity	NPC293112
0.8455	Intermediate Similarity	NPC225049
0.8455	Intermediate Similarity	NPC473635
0.8448	Intermediate Similarity	NPC469655
0.8448	Intermediate Similarity	NPC469656
0.8448	Intermediate Similarity	NPC474846
0.8443	Intermediate Similarity	NPC227397
0.8443	Intermediate Similarity	NPC11895
0.8435	Intermediate Similarity	NPC27814
0.8435	Intermediate Similarity	NPC141350
0.843	Intermediate Similarity	NPC472000
0.843	Intermediate Similarity	NPC471999
0.8421	Intermediate Similarity	NPC202524
0.8417	Intermediate Similarity	NPC77689
0.8417	Intermediate Similarity	NPC268958
0.8417	Intermediate Similarity	NPC473636
0.8413	Intermediate Similarity	NPC476193
0.8413	Intermediate Similarity	NPC254614
0.8413	Intermediate Similarity	NPC100390
0.8413	Intermediate Similarity	NPC478150
0.8413	Intermediate Similarity	NPC478153
0.8413	Intermediate Similarity	NPC478152
0.8403	Intermediate Similarity	NPC477116
0.8403	Intermediate Similarity	NPC27999
0.8403	Intermediate Similarity	NPC134430
0.8403	Intermediate Similarity	NPC478204
0.84	Intermediate Similarity	NPC264192
0.84	Intermediate Similarity	NPC231529
0.84	Intermediate Similarity	NPC477196
0.84	Intermediate Similarity	NPC476854
0.8387	Intermediate Similarity	NPC470882
0.8376	Intermediate Similarity	NPC317687
0.8374	Intermediate Similarity	NPC172154
0.8374	Intermediate Similarity	NPC81736
0.8362	Intermediate Similarity	NPC5103
0.8362	Intermediate Similarity	NPC253906
0.8361	Intermediate Similarity	NPC170538
0.8361	Intermediate Similarity	NPC222688
0.8348	Intermediate Similarity	NPC208461
0.8348	Intermediate Similarity	NPC289702
0.8347	Intermediate Similarity	NPC109973
0.8347	Intermediate Similarity	NPC251226
0.8347	Intermediate Similarity	NPC476961
0.8333	Intermediate Similarity	NPC477197
0.8333	Intermediate Similarity	NPC108581
0.8333	Intermediate Similarity	NPC476855
0.8333	Intermediate Similarity	NPC476862
0.8333	Intermediate Similarity	NPC181357
0.8333	Intermediate Similarity	NPC478205
0.8333	Intermediate Similarity	NPC476863
0.8333	Intermediate Similarity	NPC478206
0.8333	Intermediate Similarity	NPC102352
0.832	Intermediate Similarity	NPC477712
0.832	Intermediate Similarity	NPC477193
0.832	Intermediate Similarity	NPC477191
0.832	Intermediate Similarity	NPC477078
0.832	Intermediate Similarity	NPC475281
0.832	Intermediate Similarity	NPC477075
0.832	Intermediate Similarity	NPC477192
0.832	Intermediate Similarity	NPC329923
0.832	Intermediate Similarity	NPC477194
0.832	Intermediate Similarity	NPC477713

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 NPC312833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1673
0.2-0.3	3692
0.3-0.4	2226
0.4-0.5	742
0.5-0.6	326
0.6-0.7	158
0.7-0.8	106
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8348	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD6319	Approved
0.8145	Intermediate Similarity	NPD8328	Phase 3
0.7969	Intermediate Similarity	NPD7319	Approved
0.7966	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6372	Approved
0.7815	Intermediate Similarity	NPD6373	Approved
0.7805	Intermediate Similarity	NPD7115	Discovery
0.7795	Intermediate Similarity	NPD7492	Approved
0.7769	Intermediate Similarity	NPD8297	Approved
0.776	Intermediate Similarity	NPD6059	Approved
0.776	Intermediate Similarity	NPD6054	Approved
0.7752	Intermediate Similarity	NPD7736	Approved
0.7734	Intermediate Similarity	NPD6616	Approved
0.7734	Intermediate Similarity	NPD7507	Approved
0.7712	Intermediate Similarity	NPD5739	Approved
0.7712	Intermediate Similarity	NPD7128	Approved
0.7712	Intermediate Similarity	NPD6675	Approved
0.7712	Intermediate Similarity	NPD6402	Approved
0.7705	Intermediate Similarity	NPD4632	Approved
0.7698	Intermediate Similarity	NPD6015	Approved
0.7698	Intermediate Similarity	NPD6921	Approved
0.7698	Intermediate Similarity	NPD6016	Approved
0.7686	Intermediate Similarity	NPD6649	Approved
0.7686	Intermediate Similarity	NPD6650	Approved
0.7674	Intermediate Similarity	NPD7078	Approved
0.7674	Intermediate Similarity	NPD8293	Discontinued
0.7661	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD4225	Approved
0.7647	Intermediate Similarity	NPD5697	Approved
0.7647	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5701	Approved
0.7638	Intermediate Similarity	NPD6370	Approved
0.7638	Intermediate Similarity	NPD5988	Approved
0.7583	Intermediate Similarity	NPD6881	Approved
0.7583	Intermediate Similarity	NPD6899	Approved
0.7583	Intermediate Similarity	NPD6686	Approved
0.7583	Intermediate Similarity	NPD7320	Approved
0.7521	Intermediate Similarity	NPD6013	Approved
0.7521	Intermediate Similarity	NPD6014	Approved
0.7521	Intermediate Similarity	NPD6012	Approved
0.752	Intermediate Similarity	NPD6009	Approved
0.748	Intermediate Similarity	NPD6882	Approved
0.7459	Intermediate Similarity	NPD4634	Approved
0.7459	Intermediate Similarity	NPD7102	Approved
0.7459	Intermediate Similarity	NPD6883	Approved
0.7459	Intermediate Similarity	NPD7290	Approved
0.7438	Intermediate Similarity	NPD6011	Approved
0.7422	Intermediate Similarity	NPD5983	Phase 2
0.7422	Intermediate Similarity	NPD8513	Phase 3
0.7422	Intermediate Similarity	NPD8517	Approved
0.7422	Intermediate Similarity	NPD8515	Approved
0.7422	Intermediate Similarity	NPD8516	Approved
0.7402	Intermediate Similarity	NPD7516	Approved
0.7398	Intermediate Similarity	NPD8130	Phase 1
0.7398	Intermediate Similarity	NPD6847	Approved
0.7398	Intermediate Similarity	NPD6869	Approved
0.7398	Intermediate Similarity	NPD6617	Approved
0.7377	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7638	Approved
0.7323	Intermediate Similarity	NPD7327	Approved
0.7323	Intermediate Similarity	NPD7328	Approved
0.7308	Intermediate Similarity	NPD7604	Phase 2
0.7288	Intermediate Similarity	NPD7639	Approved
0.7288	Intermediate Similarity	NPD7640	Approved
0.7273	Intermediate Similarity	NPD6008	Approved
0.7265	Intermediate Similarity	NPD4755	Approved
0.7258	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD6033	Approved
0.7213	Intermediate Similarity	NPD6412	Phase 2
0.7203	Intermediate Similarity	NPD5696	Approved
0.7197	Intermediate Similarity	NPD6336	Discontinued
0.7185	Intermediate Similarity	NPD7260	Phase 2
0.7167	Intermediate Similarity	NPD5211	Phase 2
0.7165	Intermediate Similarity	NPD6274	Approved
0.7154	Intermediate Similarity	NPD8380	Approved
0.7154	Intermediate Similarity	NPD7503	Approved
0.7154	Intermediate Similarity	NPD8379	Approved
0.7154	Intermediate Similarity	NPD8378	Approved
0.7154	Intermediate Similarity	NPD8296	Approved
0.7154	Intermediate Similarity	NPD8335	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD5286	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD5285	Approved
0.7119	Intermediate Similarity	NPD7902	Approved
0.7119	Intermediate Similarity	NPD6083	Phase 2
0.7119	Intermediate Similarity	NPD6084	Phase 2
0.7077	Intermediate Similarity	NPD8294	Approved
0.7077	Intermediate Similarity	NPD8377	Approved
0.7073	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5141	Approved
0.7034	Intermediate Similarity	NPD4697	Phase 3
0.7025	Intermediate Similarity	NPD5225	Approved
0.7025	Intermediate Similarity	NPD5224	Approved
0.7025	Intermediate Similarity	NPD4633	Approved
0.7025	Intermediate Similarity	NPD5226	Approved
0.7023	Intermediate Similarity	NPD8033	Approved
0.7015	Intermediate Similarity	NPD8074	Phase 3
0.7009	Intermediate Similarity	NPD7748	Approved
0.7009	Intermediate Similarity	NPD5282	Discontinued
0.7008	Intermediate Similarity	NPD8133	Approved
0.7007	Intermediate Similarity	NPD6845	Suspended
0.7	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD7101	Approved
0.6992	Remote Similarity	NPD4767	Approved
0.6992	Remote Similarity	NPD4768	Approved
0.6984	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7515	Phase 2
0.6977	Remote Similarity	NPD6317	Approved
0.6967	Remote Similarity	NPD5175	Approved
0.6967	Remote Similarity	NPD5174	Approved
0.6949	Remote Similarity	NPD5695	Phase 3
0.6942	Remote Similarity	NPD5223	Approved
0.693	Remote Similarity	NPD3573	Approved
0.6929	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD6314	Approved
0.6923	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD6313	Approved
0.6905	Remote Similarity	NPD6371	Approved
0.6897	Remote Similarity	NPD6698	Approved
0.6897	Remote Similarity	NPD46	Approved
0.6894	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6908	Approved
0.6894	Remote Similarity	NPD6909	Approved
0.6891	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5221	Approved
0.6891	Remote Similarity	NPD5222	Approved
0.688	Remote Similarity	NPD4730	Approved
0.688	Remote Similarity	NPD4729	Approved
0.6864	Remote Similarity	NPD7900	Approved
0.6864	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3618	Phase 1
0.6838	Remote Similarity	NPD5693	Phase 1
0.6833	Remote Similarity	NPD5173	Approved
0.6829	Remote Similarity	NPD4754	Approved
0.681	Remote Similarity	NPD5328	Approved
0.6809	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5344	Discontinued
0.678	Remote Similarity	NPD6399	Phase 3
0.6772	Remote Similarity	NPD5250	Approved
0.6772	Remote Similarity	NPD5251	Approved
0.6772	Remote Similarity	NPD5247	Approved
0.6772	Remote Similarity	NPD5248	Approved
0.6772	Remote Similarity	NPD5249	Phase 3
0.6769	Remote Similarity	NPD6868	Approved
0.6754	Remote Similarity	NPD1694	Approved
0.6748	Remote Similarity	NPD7632	Discontinued
0.6746	Remote Similarity	NPD5128	Approved
0.6724	Remote Similarity	NPD6672	Approved
0.6724	Remote Similarity	NPD5737	Approved
0.6695	Remote Similarity	NPD6411	Approved
0.6695	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6639	Remote Similarity	NPD5779	Approved
0.6639	Remote Similarity	NPD4202	Approved
0.6639	Remote Similarity	NPD5778	Approved
0.6619	Remote Similarity	NPD5956	Approved
0.6589	Remote Similarity	NPD5217	Approved
0.6589	Remote Similarity	NPD5216	Approved
0.6589	Remote Similarity	NPD5215	Approved
0.6555	Remote Similarity	NPD7983	Approved
0.6552	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1700	Approved
0.6529	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6333	Approved
0.6528	Remote Similarity	NPD6334	Approved
0.6525	Remote Similarity	NPD6673	Approved
0.6525	Remote Similarity	NPD6080	Approved
0.6525	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6101	Approved
0.6525	Remote Similarity	NPD6904	Approved
0.6512	Remote Similarity	NPD5135	Approved
0.6512	Remote Similarity	NPD5169	Approved
0.6512	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5127	Approved
0.6452	Remote Similarity	NPD6648	Approved
0.645	Remote Similarity	NPD8434	Phase 2
0.6441	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6110	Phase 1
0.6434	Remote Similarity	NPD8415	Approved
0.6429	Remote Similarity	NPD8407	Phase 2
0.6423	Remote Similarity	NPD6067	Discontinued
0.6417	Remote Similarity	NPD8034	Phase 2
0.6417	Remote Similarity	NPD8035	Phase 2
0.641	Remote Similarity	NPD6684	Approved
0.641	Remote Similarity	NPD7521	Approved
0.641	Remote Similarity	NPD5330	Approved
0.641	Remote Similarity	NPD7334	Approved
0.641	Remote Similarity	NPD7146	Approved
0.641	Remote Similarity	NPD6409	Approved
0.6402	Remote Similarity	NPD7799	Discontinued
0.6387	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD3666	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