NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	496.27
Volume:	501.149
LogP:	1.995
LogD:	0.9
LogS:	-2.822
# Rotatable Bonds:	9
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	5.459
Fsp3:	0.846
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.316
MDCK Permeability:	6.763233977835625e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.905
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.756
Plasma Protein Binding (PPB):	30.196823120117188%
Volume Distribution (VD):	0.861
Pgp-substrate:	51.20957565307617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.596
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.516
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.747
CYP3A4-substrate:	0.6

ADMET: Excretion

Clearance (CL):	3.477
Half-life (T1/2):	0.595

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.381
Drug-inuced Liver Injury (DILI):	0.74
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.813
Maximum Recommended Daily Dose:	0.204
Skin Sensitization:	0.457
Carcinogencity:	0.518
Eye Corrosion:	0.474
Eye Irritation:	0.075
Respiratory Toxicity:	0.162

Download Data

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

Natural Product: NPC477442

Natural Product ID:	NPC477442
*Common Name:**	(8S,13S)-7-Oxo-9,13-epoxylabdane-3alpha,6beta,15,19-tetraol 3,6,19-triacetate
IUPAC Name:	[(1S,2R,4aS,5R,5'S,6S,8S,8aS)-2,8-diacetyloxy-5'-(2-hydroxyethyl)-1,4a,5',6-tetramethyl-7-oxospiro[2,3,4,6,8,8a-hexahydronaphthalene-5,2'-oxolane]-1-yl]methyl acetate
Synonyms:
Standard InCHIKey:	BTOUAJKAVXLICM-GCDFGGQNSA-N
Standard InCHI:	InChI=1S/C26H40O9/c1-15-20(31)21(34-18(4)30)22-24(6,14-32-16(2)28)19(33-17(3)29)8-9-25(22,7)26(15)11-10-23(5,35-26)12-13-27/h15,19,21-22,27H,8-14H2,1-7H3/t15-,19-,21-,22+,23+,24+,25+,26-/m1/s1
SMILES:	C[C@@H]1C(=O)[C@H]([C@@H]2[C@@]([C@@]13CC[C@@](O3)(C)CCO)(CC[C@H]([C@]2(C)COC(=O)C)OC(=O)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122186910
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO33600	Leonurus macranthus	Species	Lamiaceae	Eukaryota	aerial parts	Huanren, Liaoning Province, China	2013-AUG	PMID[26348503]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	20700	nM	PMID[26348503]

☑ 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 NPC477442 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	393
0.1-0.2	3027
0.2-0.3	7720
0.3-0.4	13661
0.4-0.5	6660
0.5-0.6	6302
0.6-0.7	4043
0.7-0.8	828
0.8-0.85	46
0.85-0.9	8
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477444
1.0	High Similarity	NPC477433
0.9881	High Similarity	NPC477443
0.9881	High Similarity	NPC477440
0.9524	High Similarity	NPC477441
0.9286	High Similarity	NPC477434
0.8989	High Similarity	NPC216137
0.8953	High Similarity	NPC477445
0.8696	High Similarity	NPC62407
0.8696	High Similarity	NPC287354
0.8652	High Similarity	NPC471221
0.8621	High Similarity	NPC475689
0.8556	High Similarity	NPC471459
0.8556	High Similarity	NPC67653
0.8478	Intermediate Similarity	NPC474379
0.8427	Intermediate Similarity	NPC83242
0.8427	Intermediate Similarity	NPC476717
0.8409	Intermediate Similarity	NPC237938
0.8409	Intermediate Similarity	NPC219535
0.8333	Intermediate Similarity	NPC474020
0.8315	Intermediate Similarity	NPC477205
0.8315	Intermediate Similarity	NPC473350
0.8295	Intermediate Similarity	NPC15091
0.828	Intermediate Similarity	NPC476189
0.8256	Intermediate Similarity	NPC275243
0.8242	Intermediate Similarity	NPC476435
0.8242	Intermediate Similarity	NPC236459
0.8242	Intermediate Similarity	NPC226491
0.8242	Intermediate Similarity	NPC477614
0.8235	Intermediate Similarity	NPC307865
0.8202	Intermediate Similarity	NPC471044
0.8202	Intermediate Similarity	NPC65133
0.8202	Intermediate Similarity	NPC473299
0.8202	Intermediate Similarity	NPC473336
0.8191	Intermediate Similarity	NPC247877
0.8191	Intermediate Similarity	NPC309127
0.8182	Intermediate Similarity	NPC88469
0.8161	Intermediate Similarity	NPC134227
0.8161	Intermediate Similarity	NPC125366
0.8152	Intermediate Similarity	NPC200580
0.8152	Intermediate Similarity	NPC61688
0.8068	Intermediate Similarity	NPC475743
0.8065	Intermediate Similarity	NPC475211
0.8065	Intermediate Similarity	NPC88337
0.8058	Intermediate Similarity	NPC157476
0.8043	Intermediate Similarity	NPC3032
0.8043	Intermediate Similarity	NPC473319
0.8043	Intermediate Similarity	NPC131104
0.8041	Intermediate Similarity	NPC253995
0.8022	Intermediate Similarity	NPC248216
0.8022	Intermediate Similarity	NPC120395
0.8021	Intermediate Similarity	NPC193785
0.8021	Intermediate Similarity	NPC477264
0.802	Intermediate Similarity	NPC176949
0.802	Intermediate Similarity	NPC201908
0.8	Intermediate Similarity	NPC470424
0.8	Intermediate Similarity	NPC105895
0.8	Intermediate Similarity	NPC50438
0.798	Intermediate Similarity	NPC471254
0.7979	Intermediate Similarity	NPC475878
0.7978	Intermediate Similarity	NPC477446
0.7978	Intermediate Similarity	NPC470155
0.7978	Intermediate Similarity	NPC477447
0.7938	Intermediate Similarity	NPC470632
0.7938	Intermediate Similarity	NPC74466
0.7935	Intermediate Similarity	NPC470920
0.7931	Intermediate Similarity	NPC475725
0.7912	Intermediate Similarity	NPC476715
0.79	Intermediate Similarity	NPC473406
0.79	Intermediate Similarity	NPC471253
0.79	Intermediate Similarity	NPC469985
0.7889	Intermediate Similarity	NPC476721
0.7882	Intermediate Similarity	NPC55508
0.7879	Intermediate Similarity	NPC236585
0.7879	Intermediate Similarity	NPC259654
0.7879	Intermediate Similarity	NPC298266
0.7872	Intermediate Similarity	NPC470114
0.7865	Intermediate Similarity	NPC470156
0.7865	Intermediate Similarity	NPC470154
0.7857	Intermediate Similarity	NPC474793
0.7857	Intermediate Similarity	NPC474724
0.7849	Intermediate Similarity	NPC476379
0.7835	Intermediate Similarity	NPC475765
0.7835	Intermediate Similarity	NPC235109
0.7835	Intermediate Similarity	NPC163685
0.7835	Intermediate Similarity	NPC116683
0.7835	Intermediate Similarity	NPC476728
0.7826	Intermediate Similarity	NPC474215
0.7826	Intermediate Similarity	NPC302111
0.7826	Intermediate Similarity	NPC475729
0.7822	Intermediate Similarity	NPC327093
0.7816	Intermediate Similarity	NPC143250
0.7802	Intermediate Similarity	NPC34984
0.7802	Intermediate Similarity	NPC25037
0.78	Intermediate Similarity	NPC275990
0.78	Intermediate Similarity	NPC470172
0.7789	Intermediate Similarity	NPC52756
0.7788	Intermediate Similarity	NPC100908
0.7778	Intermediate Similarity	NPC293890
0.7767	Intermediate Similarity	NPC208461
0.7767	Intermediate Similarity	NPC289702
0.7767	Intermediate Similarity	NPC316930
0.7766	Intermediate Similarity	NPC24705
0.7766	Intermediate Similarity	NPC56962
0.7765	Intermediate Similarity	NPC474755
0.7765	Intermediate Similarity	NPC109510
0.7757	Intermediate Similarity	NPC190185
0.7757	Intermediate Similarity	NPC16081
0.7757	Intermediate Similarity	NPC213084
0.7757	Intermediate Similarity	NPC173686
0.7755	Intermediate Similarity	NPC253586
0.7753	Intermediate Similarity	NPC472943
0.7753	Intermediate Similarity	NPC472951
0.7745	Intermediate Similarity	NPC50535
0.7742	Intermediate Similarity	NPC239938
0.7742	Intermediate Similarity	NPC263802
0.7736	Intermediate Similarity	NPC94509
0.7732	Intermediate Similarity	NPC477438
0.7732	Intermediate Similarity	NPC82633
0.7732	Intermediate Similarity	NPC17336
0.7732	Intermediate Similarity	NPC305808
0.7732	Intermediate Similarity	NPC477437
0.7723	Intermediate Similarity	NPC87927
0.7708	Intermediate Similarity	NPC472148
0.7708	Intermediate Similarity	NPC472147
0.7708	Intermediate Similarity	NPC147272
0.77	Intermediate Similarity	NPC46848
0.7692	Intermediate Similarity	NPC327451
0.7692	Intermediate Similarity	NPC321661
0.7692	Intermediate Similarity	NPC320475
0.7685	Intermediate Similarity	NPC146432
0.7685	Intermediate Similarity	NPC470778
0.7684	Intermediate Similarity	NPC472146
0.7684	Intermediate Similarity	NPC185529
0.7684	Intermediate Similarity	NPC77756
0.7677	Intermediate Similarity	NPC476294
0.7677	Intermediate Similarity	NPC472144
0.7677	Intermediate Similarity	NPC471038
0.767	Intermediate Similarity	NPC251824
0.767	Intermediate Similarity	NPC203974
0.767	Intermediate Similarity	NPC86852
0.7667	Intermediate Similarity	NPC328639
0.7667	Intermediate Similarity	NPC476071
0.7667	Intermediate Similarity	NPC329490
0.7664	Intermediate Similarity	NPC477465
0.7664	Intermediate Similarity	NPC470116
0.7664	Intermediate Similarity	NPC45218
0.7664	Intermediate Similarity	NPC323821
0.7664	Intermediate Similarity	NPC143268
0.7664	Intermediate Similarity	NPC268238
0.7664	Intermediate Similarity	NPC470115
0.7664	Intermediate Similarity	NPC299849
0.766	Intermediate Similarity	NPC221993
0.7653	Intermediate Similarity	NPC475785
0.7653	Intermediate Similarity	NPC219353
0.7653	Intermediate Similarity	NPC329910
0.7647	Intermediate Similarity	NPC473701
0.7647	Intermediate Similarity	NPC47281
0.7647	Intermediate Similarity	NPC473526
0.764	Intermediate Similarity	NPC320144
0.764	Intermediate Similarity	NPC201276
0.764	Intermediate Similarity	NPC80891
0.7634	Intermediate Similarity	NPC476727
0.7634	Intermediate Similarity	NPC80700
0.7634	Intermediate Similarity	NPC476726
0.7634	Intermediate Similarity	NPC472272
0.7629	Intermediate Similarity	NPC76136
0.7629	Intermediate Similarity	NPC217567
0.7629	Intermediate Similarity	NPC329713
0.7629	Intermediate Similarity	NPC477439
0.7619	Intermediate Similarity	NPC470622
0.7615	Intermediate Similarity	NPC297179
0.7614	Intermediate Similarity	NPC471151
0.7609	Intermediate Similarity	NPC181871
0.7609	Intermediate Similarity	NPC79308
0.7609	Intermediate Similarity	NPC319909
0.7609	Intermediate Similarity	NPC9060
0.7604	Intermediate Similarity	NPC474065
0.76	Intermediate Similarity	NPC108371
0.7596	Intermediate Similarity	NPC153587
0.7593	Intermediate Similarity	NPC89929
0.7593	Intermediate Similarity	NPC475490
0.7582	Intermediate Similarity	NPC289486
0.7582	Intermediate Similarity	NPC61107
0.7576	Intermediate Similarity	NPC190080
0.7576	Intermediate Similarity	NPC472273
0.7576	Intermediate Similarity	NPC472145
0.7576	Intermediate Similarity	NPC111187
0.7573	Intermediate Similarity	NPC200957
0.7573	Intermediate Similarity	NPC138908
0.7573	Intermediate Similarity	NPC28791
0.7573	Intermediate Similarity	NPC295366
0.7551	Intermediate Similarity	NPC470229
0.7551	Intermediate Similarity	NPC470031
0.7551	Intermediate Similarity	NPC470232
0.7549	Intermediate Similarity	NPC96217
0.7549	Intermediate Similarity	NPC122811
0.7547	Intermediate Similarity	NPC473062
0.7547	Intermediate Similarity	NPC470281
0.7528	Intermediate Similarity	NPC185465

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 NPC477442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	3422
0.2-0.3	3356
0.3-0.4	1133
0.4-0.5	401
0.5-0.6	224
0.6-0.7	145
0.7-0.8	42
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
0.7767	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD1700	Approved
0.7528	Intermediate Similarity	NPD6697	Approved
0.7528	Intermediate Similarity	NPD6115	Approved
0.7528	Intermediate Similarity	NPD6114	Approved
0.7528	Intermediate Similarity	NPD6118	Approved
0.7416	Intermediate Similarity	NPD6116	Phase 1
0.7386	Intermediate Similarity	NPD3703	Phase 2
0.7303	Intermediate Similarity	NPD6117	Approved
0.7238	Intermediate Similarity	NPD5739	Approved
0.7238	Intermediate Similarity	NPD6402	Approved
0.7238	Intermediate Similarity	NPD7128	Approved
0.7238	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD6372	Approved
0.7196	Intermediate Similarity	NPD6373	Approved
0.7168	Intermediate Similarity	NPD6319	Approved
0.7105	Intermediate Similarity	NPD6921	Approved
0.7103	Intermediate Similarity	NPD6881	Approved
0.7103	Intermediate Similarity	NPD6899	Approved
0.7103	Intermediate Similarity	NPD7320	Approved
0.7079	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7492	Approved
0.7064	Intermediate Similarity	NPD6650	Approved
0.7064	Intermediate Similarity	NPD6649	Approved
0.7054	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6054	Approved
0.7018	Intermediate Similarity	NPD6059	Approved
0.7009	Intermediate Similarity	NPD6616	Approved
0.7009	Intermediate Similarity	NPD5701	Approved
0.7009	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7102	Approved
0.6972	Remote Similarity	NPD6883	Approved
0.6972	Remote Similarity	NPD7290	Approved
0.6949	Remote Similarity	NPD8293	Discontinued
0.6949	Remote Similarity	NPD7078	Approved
0.6909	Remote Similarity	NPD8130	Phase 1
0.6909	Remote Similarity	NPD6617	Approved
0.6909	Remote Similarity	NPD6847	Approved
0.6909	Remote Similarity	NPD6869	Approved
0.6897	Remote Similarity	NPD6370	Approved
0.6891	Remote Similarity	NPD7736	Approved
0.6881	Remote Similarity	NPD6012	Approved
0.6881	Remote Similarity	NPD6014	Approved
0.6881	Remote Similarity	NPD6013	Approved
0.6854	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8328	Phase 3
0.6818	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3702	Approved
0.681	Remote Similarity	NPD6016	Approved
0.681	Remote Similarity	NPD6015	Approved
0.6789	Remote Similarity	NPD6011	Approved
0.6757	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5988	Approved
0.6742	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD5777	Approved
0.6637	Remote Similarity	NPD4632	Approved
0.6609	Remote Similarity	NPD6009	Approved
0.6577	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4755	Approved
0.6571	Remote Similarity	NPD6084	Phase 2
0.6571	Remote Similarity	NPD6083	Phase 2
0.6569	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD8035	Phase 2
0.6556	Remote Similarity	NPD4245	Approved
0.6556	Remote Similarity	NPD4244	Approved
0.6555	Remote Similarity	NPD7604	Phase 2
0.6552	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5983	Phase 2
0.6522	Remote Similarity	NPD6274	Approved
0.6518	Remote Similarity	NPD4634	Approved
0.6518	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5360	Phase 3
0.6514	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7101	Approved
0.6496	Remote Similarity	NPD7100	Approved
0.6484	Remote Similarity	NPD6081	Approved
0.6477	Remote Similarity	NPD4224	Phase 2
0.6475	Remote Similarity	NPD6033	Approved
0.6465	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6008	Approved
0.6449	Remote Similarity	NPD5286	Approved
0.6449	Remote Similarity	NPD4696	Approved
0.6449	Remote Similarity	NPD4700	Approved
0.6449	Remote Similarity	NPD5285	Approved
0.6446	Remote Similarity	NPD6336	Discontinued
0.6444	Remote Similarity	NPD3698	Phase 2
0.641	Remote Similarity	NPD6335	Approved
0.6387	Remote Similarity	NPD6908	Approved
0.6387	Remote Similarity	NPD6909	Approved
0.6355	Remote Similarity	NPD7638	Approved
0.6348	Remote Similarity	NPD8133	Approved
0.6346	Remote Similarity	NPD6399	Phase 3
0.6333	Remote Similarity	NPD229	Approved
0.633	Remote Similarity	NPD5226	Approved
0.633	Remote Similarity	NPD4633	Approved
0.633	Remote Similarity	NPD5211	Phase 2
0.633	Remote Similarity	NPD5224	Approved
0.633	Remote Similarity	NPD5225	Approved
0.6325	Remote Similarity	NPD6317	Approved
0.6306	Remote Similarity	NPD4768	Approved
0.6306	Remote Similarity	NPD4767	Approved
0.6296	Remote Similarity	NPD7639	Approved
0.6296	Remote Similarity	NPD7640	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6289	Remote Similarity	NPD6928	Phase 2
0.6286	Remote Similarity	NPD7748	Approved
0.6273	Remote Similarity	NPD5174	Approved
0.6273	Remote Similarity	NPD5175	Approved
0.6271	Remote Similarity	NPD6313	Approved
0.6271	Remote Similarity	NPD6314	Approved
0.6264	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD3669	Approved
0.6263	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7902	Approved
0.625	Remote Similarity	NPD4238	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD4802	Phase 2
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD3671	Phase 1
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD5223	Approved
0.6226	Remote Similarity	NPD5695	Phase 3
0.6224	Remote Similarity	NPD1779	Approved
0.6224	Remote Similarity	NPD1780	Approved
0.6216	Remote Similarity	NPD5141	Approved
0.6214	Remote Similarity	NPD5328	Approved
0.6204	Remote Similarity	NPD5696	Approved
0.6196	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4730	Approved
0.6195	Remote Similarity	NPD4729	Approved
0.619	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD5778	Approved
0.6182	Remote Similarity	NPD7632	Discontinued
0.6179	Remote Similarity	NPD7507	Approved
0.6168	Remote Similarity	NPD5221	Approved
0.6168	Remote Similarity	NPD4697	Phase 3
0.6168	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5222	Approved
0.6147	Remote Similarity	NPD8418	Phase 2
0.6132	Remote Similarity	NPD5282	Discontinued
0.6129	Remote Similarity	NPD4758	Discontinued
0.6126	Remote Similarity	NPD4754	Approved
0.6117	Remote Similarity	NPD6672	Approved
0.6117	Remote Similarity	NPD5737	Approved
0.6116	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5173	Approved
0.6095	Remote Similarity	NPD6079	Approved
0.6087	Remote Similarity	NPD5250	Approved
0.6087	Remote Similarity	NPD5248	Approved
0.6087	Remote Similarity	NPD5247	Approved
0.6087	Remote Similarity	NPD5251	Approved
0.6087	Remote Similarity	NPD5249	Phase 3
0.6082	Remote Similarity	NPD5364	Discontinued
0.6067	Remote Similarity	NPD7909	Approved
0.6058	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6101	Approved
0.6055	Remote Similarity	NPD4225	Approved
0.6053	Remote Similarity	NPD5128	Approved
0.6053	Remote Similarity	NPD6686	Approved
0.605	Remote Similarity	NPD7115	Discovery
0.6038	Remote Similarity	NPD8171	Discontinued
0.6036	Remote Similarity	NPD8138	Approved
0.6036	Remote Similarity	NPD8083	Approved
0.6036	Remote Similarity	NPD8139	Approved
0.6036	Remote Similarity	NPD8085	Approved
0.6036	Remote Similarity	NPD8084	Approved
0.6036	Remote Similarity	NPD8082	Approved
0.6036	Remote Similarity	NPD8086	Approved
0.6	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8275	Approved
0.5982	Remote Similarity	NPD8276	Approved
0.5981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7900	Approved
0.5966	Remote Similarity	NPD6940	Discontinued
0.5965	Remote Similarity	NPD6412	Phase 2
0.5952	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD8081	Approved
0.5922	Remote Similarity	NPD6098	Approved
0.5922	Remote Similarity	NPD3618	Phase 1
0.5909	Remote Similarity	NPD6334	Approved
0.5909	Remote Similarity	NPD6333	Approved
0.5905	Remote Similarity	NPD6904	Approved
0.5905	Remote Similarity	NPD4753	Phase 2
0.5905	Remote Similarity	NPD6080	Approved
0.5905	Remote Similarity	NPD6673	Approved
0.5897	Remote Similarity	NPD5215	Approved
0.5897	Remote Similarity	NPD5217	Approved
0.5897	Remote Similarity	NPD5216	Approved
0.5893	Remote Similarity	NPD8301	Approved
0.5893	Remote Similarity	NPD8300	Approved
0.5889	Remote Similarity	NPD371	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