NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	592.24
Volume:	560.97
LogP:	2.869
LogD:	1.3
LogS:	-3.939
# Rotatable Bonds:	10
TPSA:	173.32
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.218
Synthetic Accessibility Score:	5.484
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.945
MDCK Permeability:	1.17E-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.319
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	99.40%
Volume Distribution (VD):	1.555
Pgp-substrate:	2.58%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.73
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	1.389
Half-life (T1/2):	0.018

ADMET: Toxicity

hERG Blockers:	0.516
Human Hepatotoxicity (H-HT):	0.946
Drug-inuced Liver Injury (DILI):	0.324
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.584
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.961
Carcinogencity:	0.89
Eye Corrosion:	0.005
Eye Irritation:	0.024
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC477605

Natural Product ID:	NPC477605
*Common Name:**	disodium;[(2R,3R,4S,10R,13S,17R)-2,4-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-1-sulfonatooxyheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
IUPAC Name:	disodium;[(2R,3R,4S,10R,13S,17R)-2,4-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-1-sulfonatooxyheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
Synonyms:
Standard InCHIKey:	VWQVKLMCGUIETE-PZBSYZMPSA-L
Standard InCHI:	InChI=1S/C27H46O10S2.2Na/c1-16(2)6-5-7-17(15-36-38(30,31)32)19-10-11-20-18-8-9-22-24(29)25(37-39(33,34)35)23(28)14-27(22,4)21(18)12-13-26(19,20)3;;/h9,16-21,23-25,28-29H,5-8,10-15H2,1-4H3,(H,30,31,32)(H,33,34,35);;/q;2*+1/p-2/t17-,18?,19+,20?,21?,23+,24-,25+,26+,27+;;/m0../s1
SMILES:	CC(C)CCC[C@@H](COS(=O)(=O)[O-])[C@H]1CCC2[C@@]1(CCC3C2CC=C4[C@@]3(C[C@H]([C@H]([C@H]4O)OS(=O)(=O)[O-])O)C)C.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44378987
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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
NPO33559	Ophiosphate gigaes	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8145229]
NPO33559	Ophiosphate gigaes	Species	n.a.	n.a.	n.a.	Gondwana, Italy	1989-1990	PMID[8145229]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	20	nM	PMID[8145229]

☑ 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 NPC477605 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	186
0.1-0.2	1604
0.2-0.3	5378
0.3-0.4	14548
0.4-0.5	9909
0.5-0.6	6231
0.6-0.7	4072
0.7-0.8	685
0.8-0.85	55
0.85-0.9	22
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.954	High Similarity	NPC477606
0.9195	High Similarity	NPC477604
0.9091	High Similarity	NPC475313
0.8989	High Similarity	NPC474668
0.8901	High Similarity	NPC97404
0.8901	High Similarity	NPC41554
0.8889	High Similarity	NPC470361
0.8851	High Similarity	NPC317458
0.883	High Similarity	NPC477226
0.8791	High Similarity	NPC329596
0.8791	High Similarity	NPC204188
0.8791	High Similarity	NPC11216
0.8791	High Similarity	NPC80561
0.8791	High Similarity	NPC3345
0.8791	High Similarity	NPC291484
0.8764	High Similarity	NPC6391
0.875	High Similarity	NPC185568
0.8667	High Similarity	NPC477600
0.8636	High Similarity	NPC474634
0.8621	High Similarity	NPC473534
0.8621	High Similarity	NPC209620
0.8621	High Similarity	NPC23852
0.8571	High Similarity	NPC133588
0.8556	High Similarity	NPC152808
0.8556	High Similarity	NPC293287
0.8556	High Similarity	NPC261266
0.8539	High Similarity	NPC478102
0.8526	High Similarity	NPC288970
0.8523	High Similarity	NPC50964
0.8523	High Similarity	NPC101462
0.8495	Intermediate Similarity	NPC275671
0.8462	Intermediate Similarity	NPC470620
0.8444	Intermediate Similarity	NPC470360
0.8409	Intermediate Similarity	NPC470383
0.8409	Intermediate Similarity	NPC474531
0.8404	Intermediate Similarity	NPC310013
0.8391	Intermediate Similarity	NPC30986
0.8391	Intermediate Similarity	NPC47982
0.8391	Intermediate Similarity	NPC143182
0.8391	Intermediate Similarity	NPC84694
0.8391	Intermediate Similarity	NPC109546
0.8391	Intermediate Similarity	NPC209430
0.8391	Intermediate Similarity	NPC28862
0.8391	Intermediate Similarity	NPC81306
0.837	Intermediate Similarity	NPC280556
0.837	Intermediate Similarity	NPC67872
0.8352	Intermediate Similarity	NPC269058
0.8352	Intermediate Similarity	NPC94462
0.8352	Intermediate Similarity	NPC299068
0.8352	Intermediate Similarity	NPC71520
0.8352	Intermediate Similarity	NPC478094
0.8333	Intermediate Similarity	NPC205845
0.8316	Intermediate Similarity	NPC127718
0.8316	Intermediate Similarity	NPC65402
0.8315	Intermediate Similarity	NPC30166
0.8315	Intermediate Similarity	NPC477599
0.8295	Intermediate Similarity	NPC236112
0.8295	Intermediate Similarity	NPC234193
0.828	Intermediate Similarity	NPC187785
0.828	Intermediate Similarity	NPC105495
0.828	Intermediate Similarity	NPC259875
0.8276	Intermediate Similarity	NPC475337
0.8276	Intermediate Similarity	NPC474216
0.8276	Intermediate Similarity	NPC87604
0.8242	Intermediate Similarity	NPC266511
0.8229	Intermediate Similarity	NPC8774
0.8222	Intermediate Similarity	NPC320548
0.8202	Intermediate Similarity	NPC264245
0.8191	Intermediate Similarity	NPC473956
0.8191	Intermediate Similarity	NPC475751
0.8191	Intermediate Similarity	NPC295668
0.8182	Intermediate Similarity	NPC328714
0.8172	Intermediate Similarity	NPC475664
0.8144	Intermediate Similarity	NPC210717
0.8144	Intermediate Similarity	NPC103165
0.8144	Intermediate Similarity	NPC12103
0.8144	Intermediate Similarity	NPC72204
0.8144	Intermediate Similarity	NPC227583
0.8144	Intermediate Similarity	NPC98457
0.8132	Intermediate Similarity	NPC124172
0.8132	Intermediate Similarity	NPC469878
0.8111	Intermediate Similarity	NPC189972
0.8111	Intermediate Similarity	NPC470614
0.8111	Intermediate Similarity	NPC1272
0.8111	Intermediate Similarity	NPC7988
0.8111	Intermediate Similarity	NPC49964
0.8095	Intermediate Similarity	NPC477050
0.809	Intermediate Similarity	NPC164840
0.809	Intermediate Similarity	NPC241290
0.809	Intermediate Similarity	NPC209944
0.809	Intermediate Similarity	NPC26117
0.8085	Intermediate Similarity	NPC109744
0.8068	Intermediate Similarity	NPC473943
0.8068	Intermediate Similarity	NPC83351
0.8068	Intermediate Similarity	NPC167891
0.8065	Intermediate Similarity	NPC474657
0.8065	Intermediate Similarity	NPC149224
0.8065	Intermediate Similarity	NPC186145
0.8061	Intermediate Similarity	NPC316604
0.8061	Intermediate Similarity	NPC476893
0.8061	Intermediate Similarity	NPC261807
0.8046	Intermediate Similarity	NPC321381
0.8046	Intermediate Similarity	NPC244488
0.8046	Intermediate Similarity	NPC247325
0.8046	Intermediate Similarity	NPC321016
0.8046	Intermediate Similarity	NPC107059
0.8041	Intermediate Similarity	NPC476894
0.8022	Intermediate Similarity	NPC470384
0.8022	Intermediate Similarity	NPC475789
0.8022	Intermediate Similarity	NPC85095
0.8022	Intermediate Similarity	NPC113978
0.8022	Intermediate Similarity	NPC211135
0.8022	Intermediate Similarity	NPC207013
0.8022	Intermediate Similarity	NPC216420
0.802	Intermediate Similarity	NPC474124
0.8	Intermediate Similarity	NPC7505
0.8	Intermediate Similarity	NPC47761
0.8	Intermediate Similarity	NPC245410
0.8	Intermediate Similarity	NPC474683
0.8	Intermediate Similarity	NPC14380
0.8	Intermediate Similarity	NPC270511
0.8	Intermediate Similarity	NPC476646
0.8	Intermediate Similarity	NPC470390
0.8	Intermediate Similarity	NPC475617
0.8	Intermediate Similarity	NPC192437
0.8	Intermediate Similarity	NPC249423
0.8	Intermediate Similarity	NPC320525
0.8	Intermediate Similarity	NPC474752
0.8	Intermediate Similarity	NPC474759
0.8	Intermediate Similarity	NPC474731
0.8	Intermediate Similarity	NPC82986
0.798	Intermediate Similarity	NPC476895
0.7957	Intermediate Similarity	NPC24277
0.7957	Intermediate Similarity	NPC201273
0.7957	Intermediate Similarity	NPC139724
0.7957	Intermediate Similarity	NPC121981
0.7957	Intermediate Similarity	NPC237344
0.7955	Intermediate Similarity	NPC318495
0.7955	Intermediate Similarity	NPC477924
0.7955	Intermediate Similarity	NPC155986
0.7955	Intermediate Similarity	NPC198968
0.7941	Intermediate Similarity	NPC75608
0.7941	Intermediate Similarity	NPC473543
0.7938	Intermediate Similarity	NPC144202
0.7935	Intermediate Similarity	NPC238485
0.7935	Intermediate Similarity	NPC209802
0.7935	Intermediate Similarity	NPC474047
0.7935	Intermediate Similarity	NPC255882
0.7931	Intermediate Similarity	NPC134847
0.7931	Intermediate Similarity	NPC304309
0.7931	Intermediate Similarity	NPC141071
0.7931	Intermediate Similarity	NPC22105
0.7931	Intermediate Similarity	NPC288035
0.7931	Intermediate Similarity	NPC28657
0.7931	Intermediate Similarity	NPC162742
0.7931	Intermediate Similarity	NPC230301
0.7931	Intermediate Similarity	NPC285893
0.7931	Intermediate Similarity	NPC257347
0.7931	Intermediate Similarity	NPC136188
0.7931	Intermediate Similarity	NPC471723
0.7921	Intermediate Similarity	NPC475344
0.7921	Intermediate Similarity	NPC476471
0.7917	Intermediate Similarity	NPC210268
0.7917	Intermediate Similarity	NPC114389
0.7912	Intermediate Similarity	NPC296701
0.7912	Intermediate Similarity	NPC202389
0.7912	Intermediate Similarity	NPC248886
0.7912	Intermediate Similarity	NPC87489
0.7912	Intermediate Similarity	NPC470049
0.7912	Intermediate Similarity	NPC218616
0.7895	Intermediate Similarity	NPC101886
0.7889	Intermediate Similarity	NPC13554
0.7889	Intermediate Similarity	NPC324772
0.7889	Intermediate Similarity	NPC287749
0.7889	Intermediate Similarity	NPC96362
0.7889	Intermediate Similarity	NPC22403
0.7865	Intermediate Similarity	NPC477522
0.7865	Intermediate Similarity	NPC275910
0.7849	Intermediate Similarity	NPC318390
0.7849	Intermediate Similarity	NPC274448
0.7843	Intermediate Similarity	NPC470601
0.7843	Intermediate Similarity	NPC473523
0.7841	Intermediate Similarity	NPC189883
0.7841	Intermediate Similarity	NPC300324
0.7841	Intermediate Similarity	NPC477925
0.7841	Intermediate Similarity	NPC129165
0.7841	Intermediate Similarity	NPC113733
0.7841	Intermediate Similarity	NPC134330
0.7841	Intermediate Similarity	NPC253190
0.7841	Intermediate Similarity	NPC240604
0.7841	Intermediate Similarity	NPC274079
0.7835	Intermediate Similarity	NPC27531
0.7835	Intermediate Similarity	NPC119379
0.7835	Intermediate Similarity	NPC98193
0.7835	Intermediate Similarity	NPC137461
0.7826	Intermediate Similarity	NPC110778
0.7822	Intermediate Similarity	NPC476896
0.7822	Intermediate Similarity	NPC470434
0.7816	Intermediate Similarity	NPC306727
0.7816	Intermediate Similarity	NPC469534

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 NPC477605 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1744
0.2-0.3	4324
0.3-0.4	2097
0.4-0.5	432
0.5-0.6	218
0.6-0.7	156
0.7-0.8	27
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
0.8065	Intermediate Similarity	NPD7524	Approved
0.7978	Intermediate Similarity	NPD6929	Approved
0.7931	Intermediate Similarity	NPD7339	Approved
0.7931	Intermediate Similarity	NPD6942	Approved
0.7889	Intermediate Similarity	NPD6930	Phase 2
0.7889	Intermediate Similarity	NPD6931	Approved
0.7872	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6695	Phase 3
0.7753	Intermediate Similarity	NPD5776	Phase 2
0.7753	Intermediate Similarity	NPD6925	Approved
0.7742	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7514	Phase 3
0.7692	Intermediate Similarity	NPD7525	Registered
0.7667	Intermediate Similarity	NPD7145	Approved
0.764	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6902	Approved
0.75	Intermediate Similarity	NPD7750	Discontinued
0.75	Intermediate Similarity	NPD7332	Phase 2
0.7474	Intermediate Similarity	NPD6893	Approved
0.7444	Intermediate Similarity	NPD6933	Approved
0.7368	Intermediate Similarity	NPD4786	Approved
0.7363	Intermediate Similarity	NPD6932	Approved
0.7234	Intermediate Similarity	NPD6898	Phase 1
0.7222	Intermediate Similarity	NPD6924	Approved
0.7222	Intermediate Similarity	NPD6926	Approved
0.7204	Intermediate Similarity	NPD6683	Phase 2
0.7204	Intermediate Similarity	NPD7645	Phase 2
0.72	Intermediate Similarity	NPD7087	Discontinued
0.7188	Intermediate Similarity	NPD3668	Phase 3
0.7158	Intermediate Similarity	NPD3667	Approved
0.71	Intermediate Similarity	NPD7136	Phase 2
0.7048	Intermediate Similarity	NPD7639	Approved
0.7048	Intermediate Similarity	NPD7640	Approved
0.7033	Intermediate Similarity	NPD4784	Approved
0.7033	Intermediate Similarity	NPD4785	Approved
0.703	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD7151	Approved
0.7	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD7150	Approved
0.7	Intermediate Similarity	NPD7152	Approved
0.7	Intermediate Similarity	NPD4243	Approved
0.6966	Remote Similarity	NPD6923	Approved
0.6966	Remote Similarity	NPD6922	Approved
0.6957	Remote Similarity	NPD8264	Approved
0.6952	Remote Similarity	NPD7638	Approved
0.6947	Remote Similarity	NPD4748	Discontinued
0.6915	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7516	Approved
0.6889	Remote Similarity	NPD7143	Approved
0.6889	Remote Similarity	NPD7144	Approved
0.6869	Remote Similarity	NPD3618	Phase 1
0.6863	Remote Similarity	NPD6079	Approved
0.6822	Remote Similarity	NPD4159	Approved
0.681	Remote Similarity	NPD7327	Approved
0.681	Remote Similarity	NPD7328	Approved
0.6796	Remote Similarity	NPD6399	Phase 3
0.6778	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7509	Discontinued
0.6759	Remote Similarity	NPD5211	Phase 2
0.6724	Remote Similarity	NPD7115	Discovery
0.6698	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6639	Remote Similarity	NPD8379	Approved
0.6639	Remote Similarity	NPD8033	Approved
0.6639	Remote Similarity	NPD8335	Approved
0.6639	Remote Similarity	NPD8296	Approved
0.6639	Remote Similarity	NPD8380	Approved
0.6639	Remote Similarity	NPD8378	Approved
0.6637	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD4225	Approved
0.6636	Remote Similarity	NPD5141	Approved
0.6635	Remote Similarity	NPD4202	Approved
0.6604	Remote Similarity	NPD5221	Approved
0.6604	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5222	Approved
0.6604	Remote Similarity	NPD4697	Phase 3
0.6596	Remote Similarity	NPD4190	Phase 3
0.6596	Remote Similarity	NPD5275	Approved
0.6577	Remote Similarity	NPD6640	Phase 3
0.6574	Remote Similarity	NPD5286	Approved
0.6574	Remote Similarity	NPD4700	Approved
0.6574	Remote Similarity	NPD4696	Approved
0.6574	Remote Similarity	NPD5285	Approved
0.6555	Remote Similarity	NPD8294	Approved
0.6555	Remote Similarity	NPD8377	Approved
0.6542	Remote Similarity	NPD5173	Approved
0.6518	Remote Similarity	NPD6412	Phase 2
0.6505	Remote Similarity	NPD6051	Approved
0.65	Remote Similarity	NPD7503	Approved
0.6495	Remote Similarity	NPD4195	Approved
0.6481	Remote Similarity	NPD5290	Discontinued
0.6455	Remote Similarity	NPD7632	Discontinued
0.6455	Remote Similarity	NPD5224	Approved
0.6455	Remote Similarity	NPD5225	Approved
0.6455	Remote Similarity	NPD5226	Approved
0.6455	Remote Similarity	NPD4633	Approved
0.6436	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD4768	Approved
0.6429	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6404	Remote Similarity	NPD6373	Approved
0.6404	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6372	Approved
0.6396	Remote Similarity	NPD5175	Approved
0.6396	Remote Similarity	NPD5174	Approved
0.6396	Remote Similarity	NPD4754	Approved
0.6389	Remote Similarity	NPD6083	Phase 2
0.6389	Remote Similarity	NPD6084	Phase 2
0.6381	Remote Similarity	NPD7515	Phase 2
0.6379	Remote Similarity	NPD8297	Approved
0.6373	Remote Similarity	NPD5279	Phase 3
0.6364	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD5344	Discontinued
0.6355	Remote Similarity	NPD5210	Approved
0.6355	Remote Similarity	NPD4629	Approved
0.6325	Remote Similarity	NPD4632	Approved
0.6316	Remote Similarity	NPD6686	Approved
0.6316	Remote Similarity	NPD6881	Approved
0.6316	Remote Similarity	NPD4729	Approved
0.6316	Remote Similarity	NPD4730	Approved
0.6316	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD6899	Approved
0.63	Remote Similarity	NPD4221	Approved
0.63	Remote Similarity	NPD4223	Phase 3
0.6293	Remote Similarity	NPD6649	Approved
0.6293	Remote Similarity	NPD6650	Approved
0.629	Remote Similarity	NPD7507	Approved
0.6281	Remote Similarity	NPD6319	Approved
0.6275	Remote Similarity	NPD5329	Approved
0.627	Remote Similarity	NPD7319	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6228	Remote Similarity	NPD5701	Approved
0.6228	Remote Similarity	NPD5697	Approved
0.6207	Remote Similarity	NPD5251	Approved
0.6207	Remote Similarity	NPD7290	Approved
0.6207	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6883	Approved
0.6207	Remote Similarity	NPD5250	Approved
0.6207	Remote Similarity	NPD5247	Approved
0.6207	Remote Similarity	NPD5249	Phase 3
0.6207	Remote Similarity	NPD7102	Approved
0.6207	Remote Similarity	NPD5248	Approved
0.6176	Remote Similarity	NPD4197	Approved
0.6174	Remote Similarity	NPD5128	Approved
0.6168	Remote Similarity	NPD5779	Approved
0.6168	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD6869	Approved
0.6154	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6847	Approved
0.6154	Remote Similarity	NPD6617	Approved
0.6148	Remote Similarity	NPD6054	Approved
0.6148	Remote Similarity	NPD6059	Approved
0.6148	Remote Similarity	NPD7741	Discontinued
0.614	Remote Similarity	NPD7333	Discontinued
0.6121	Remote Similarity	NPD6014	Approved
0.6121	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6012	Approved
0.6121	Remote Similarity	NPD6013	Approved
0.6111	Remote Similarity	NPD7748	Approved
0.6095	Remote Similarity	NPD5737	Approved
0.6095	Remote Similarity	NPD6672	Approved
0.6078	Remote Similarity	NPD4788	Approved
0.6075	Remote Similarity	NPD8034	Phase 2
0.6075	Remote Similarity	NPD8035	Phase 2
0.6068	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5135	Approved
0.6061	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6118	Approved
0.6061	Remote Similarity	NPD6114	Approved
0.6061	Remote Similarity	NPD6115	Approved
0.6061	Remote Similarity	NPD6697	Approved
0.6058	Remote Similarity	NPD4688	Approved
0.6058	Remote Similarity	NPD4690	Approved
0.6058	Remote Similarity	NPD7146	Approved
0.6058	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5205	Approved
0.6058	Remote Similarity	NPD4623	Approved
0.6058	Remote Similarity	NPD6409	Approved
0.6058	Remote Similarity	NPD7334	Approved
0.6058	Remote Similarity	NPD5330	Approved
0.6058	Remote Similarity	NPD6684	Approved
0.6058	Remote Similarity	NPD4689	Approved
0.6058	Remote Similarity	NPD4519	Discontinued
0.6058	Remote Similarity	NPD7521	Approved
0.6058	Remote Similarity	NPD4693	Phase 3
0.6058	Remote Similarity	NPD4138	Approved
0.6055	Remote Similarity	NPD5695	Phase 3
0.605	Remote Similarity	NPD8133	Approved
0.6048	Remote Similarity	NPD6370	Approved
0.6042	Remote Similarity	NPD4732	Discontinued
0.6036	Remote Similarity	NPD5696	Approved
0.6034	Remote Similarity	NPD6011	Approved
0.6034	Remote Similarity	NPD5168	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