NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	703.34
Volume:	680.028
LogP:	0.595
LogD:	0.557
LogS:	-1.934
# Rotatable Bonds:	9
TPSA:	226.5
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.099
Synthetic Accessibility Score:	6.372
Fsp3:	0.882
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.818
MDCK Permeability:	4.317098137107678e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.213
Human Intestinal Absorption (HIA):	0.919
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	80.18575286865234%
Volume Distribution (VD):	0.686
Pgp-substrate:	5.339594841003418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.517
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	0.959
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.365
Human Hepatotoxicity (H-HT):	0.826
Drug-inuced Liver Injury (DILI):	0.352
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.051
Carcinogencity:	0.093
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC477050

Natural Product ID:	NPC477050
*Common Name:**	sodium;[(3S,6R,8S,10R,13R,15R,16R,17R)-6,8,16-trihydroxy-17-[(E,2R,5R)-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-10,13-dimethyl-3-(3,4,5-trihydroxy-2-methoxyoxan-2-yl)-1,2,3,6,7,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-15-yl] sulfate
IUPAC Name:	sodium;[(3S,6R,8S,10R,13R,15R,16R,17R)-6,8,16-trihydroxy-17-[(E,2R,5R)-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-10,13-dimethyl-3-(3,4,5-trihydroxy-2-methoxyoxan-2-yl)-1,2,3,6,7,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-15-yl] sulfate
Synonyms:
Standard InCHIKey:	ZRNVKQAXIVTXCX-SIHMLIBKSA-M
Standard InCHI:	InChI=1S/C34H56O13S.Na/c1-17(2)19(15-35)8-7-18(3)25-27(39)28(47-48(42,43)44)29-32(25,5)12-10-24-31(4)11-9-20(13-21(31)22(36)14-33(24,29)41)34(45-6)30(40)26(38)23(37)16-46-34;/h7-8,13,17-20,22-30,35-41H,9-12,14-16H2,1-6H3,(H,42,43,44);/q;+1/p-1/b8-7+;/t18-,19-,20+,22-,23?,24?,25+,26?,27-,28+,29?,30?,31+,32-,33+,34?;/m1./s1
SMILES:	C[C@H](/C=C/[C@H](CO)C(C)C)[C@H]1[C@H]([C@@H](C2[C@@]1(CCC3[C@]2(C[C@H](C4=C[C@H](CC[C@]34C)C5(C(C(C(CO5)O)O)O)OC)O)O)C)OS(=O)(=O)[O-])O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44379113
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO33540	Echinaster brasiliensis	Species	Echinasteridae	Eukaryota	n.a.	Grand Bahama Island	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	2

Activity Type	# Activity
Organism	2

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	=	64000	nM	PMID[8145229]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	IC50	>	64000	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 NPC477050 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	262
0.1-0.2	1785
0.2-0.3	5343
0.3-0.4	12359
0.4-0.5	10597
0.5-0.6	5936
0.6-0.7	4565
0.7-0.8	1651
0.8-0.85	169
0.85-0.9	27
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC216595
0.9252	High Similarity	NPC473567
0.9074	High Similarity	NPC475354
0.8952	High Similarity	NPC75608
0.8868	High Similarity	NPC474015
0.8868	High Similarity	NPC472899
0.8868	High Similarity	NPC472900
0.8868	High Similarity	NPC472898
0.8857	High Similarity	NPC475701
0.8796	High Similarity	NPC128133
0.8785	High Similarity	NPC33053
0.8785	High Similarity	NPC226642
0.8774	High Similarity	NPC474464
0.8727	High Similarity	NPC475312
0.8716	High Similarity	NPC65155
0.8716	High Similarity	NPC170974
0.8716	High Similarity	NPC191439
0.8716	High Similarity	NPC103627
0.8704	High Similarity	NPC472897
0.8704	High Similarity	NPC472896
0.8692	High Similarity	NPC473923
0.8692	High Similarity	NPC474569
0.8692	High Similarity	NPC473476
0.8692	High Similarity	NPC242748
0.8692	High Similarity	NPC26798
0.8679	High Similarity	NPC473198
0.8667	High Similarity	NPC470434
0.8654	High Similarity	NPC476895
0.8649	High Similarity	NPC307642
0.8636	High Similarity	NPC197231
0.8624	High Similarity	NPC28844
0.8624	High Similarity	NPC473328
0.8624	High Similarity	NPC473318
0.8611	High Similarity	NPC231340
0.8611	High Similarity	NPC473469
0.8598	High Similarity	NPC471111
0.8598	High Similarity	NPC187400
0.8598	High Similarity	NPC470885
0.8598	High Similarity	NPC312774
0.8598	High Similarity	NPC93352
0.8598	High Similarity	NPC221562
0.8585	High Similarity	NPC136816
0.8571	High Similarity	NPC469942
0.8559	High Similarity	NPC231797
0.8559	High Similarity	NPC19888
0.8558	High Similarity	NPC476893
0.8545	High Similarity	NPC141433
0.8532	High Similarity	NPC476539
0.8532	High Similarity	NPC475634
0.8532	High Similarity	NPC476541
0.8532	High Similarity	NPC235824
0.8532	High Similarity	NPC476538
0.8532	High Similarity	NPC476540
0.8491	Intermediate Similarity	NPC47566
0.8491	Intermediate Similarity	NPC88000
0.8491	Intermediate Similarity	NPC4831
0.8491	Intermediate Similarity	NPC309425
0.8491	Intermediate Similarity	NPC476896
0.8491	Intermediate Similarity	NPC474022
0.8491	Intermediate Similarity	NPC160734
0.8491	Intermediate Similarity	NPC472023
0.8491	Intermediate Similarity	NPC129372
0.8482	Intermediate Similarity	NPC51154
0.8476	Intermediate Similarity	NPC158088
0.8468	Intermediate Similarity	NPC65034
0.8468	Intermediate Similarity	NPC208189
0.8468	Intermediate Similarity	NPC13190
0.8455	Intermediate Similarity	NPC42482
0.8455	Intermediate Similarity	NPC477026
0.8455	Intermediate Similarity	NPC40440
0.8455	Intermediate Similarity	NPC475670
0.8455	Intermediate Similarity	NPC70204
0.8455	Intermediate Similarity	NPC306131
0.8455	Intermediate Similarity	NPC472901
0.8455	Intermediate Similarity	NPC474573
0.8455	Intermediate Similarity	NPC477027
0.844	Intermediate Similarity	NPC190395
0.8426	Intermediate Similarity	NPC475365
0.8411	Intermediate Similarity	NPC272015
0.8396	Intermediate Similarity	NPC91497
0.8396	Intermediate Similarity	NPC471242
0.8396	Intermediate Similarity	NPC7341
0.8396	Intermediate Similarity	NPC473200
0.8396	Intermediate Similarity	NPC64348
0.8393	Intermediate Similarity	NPC112274
0.8381	Intermediate Similarity	NPC477226
0.8381	Intermediate Similarity	NPC177818
0.8381	Intermediate Similarity	NPC243728
0.8381	Intermediate Similarity	NPC240372
0.8381	Intermediate Similarity	NPC473890
0.8378	Intermediate Similarity	NPC472717
0.8365	Intermediate Similarity	NPC476894
0.8364	Intermediate Similarity	NPC7213
0.8349	Intermediate Similarity	NPC309448
0.8349	Intermediate Similarity	NPC181845
0.8348	Intermediate Similarity	NPC476692
0.8348	Intermediate Similarity	NPC476691
0.8333	Intermediate Similarity	NPC473020
0.8333	Intermediate Similarity	NPC155010
0.8333	Intermediate Similarity	NPC189852
0.8333	Intermediate Similarity	NPC213190
0.8333	Intermediate Similarity	NPC31907
0.8333	Intermediate Similarity	NPC157659
0.8333	Intermediate Similarity	NPC472252
0.8333	Intermediate Similarity	NPC146652
0.8333	Intermediate Similarity	NPC114874
0.8333	Intermediate Similarity	NPC16520
0.8333	Intermediate Similarity	NPC286969
0.8333	Intermediate Similarity	NPC211879
0.8333	Intermediate Similarity	NPC120123
0.8333	Intermediate Similarity	NPC8039
0.8333	Intermediate Similarity	NPC131479
0.8333	Intermediate Similarity	NPC245280
0.8319	Intermediate Similarity	NPC476671
0.8318	Intermediate Similarity	NPC285231
0.8318	Intermediate Similarity	NPC176406
0.8318	Intermediate Similarity	NPC267510
0.8318	Intermediate Similarity	NPC21568
0.8304	Intermediate Similarity	NPC477028
0.8304	Intermediate Similarity	NPC477032
0.8304	Intermediate Similarity	NPC475247
0.8304	Intermediate Similarity	NPC114188
0.8304	Intermediate Similarity	NPC294129
0.8304	Intermediate Similarity	NPC473021
0.8304	Intermediate Similarity	NPC124677
0.8304	Intermediate Similarity	NPC472715
0.8304	Intermediate Similarity	NPC472987
0.8302	Intermediate Similarity	NPC280825
0.8302	Intermediate Similarity	NPC275865
0.8302	Intermediate Similarity	NPC234287
0.8288	Intermediate Similarity	NPC157530
0.8288	Intermediate Similarity	NPC476835
0.8288	Intermediate Similarity	NPC14630
0.8288	Intermediate Similarity	NPC302057
0.8288	Intermediate Similarity	NPC250089
0.8286	Intermediate Similarity	NPC207617
0.8286	Intermediate Similarity	NPC90583
0.8286	Intermediate Similarity	NPC288970
0.8286	Intermediate Similarity	NPC98457
0.8286	Intermediate Similarity	NPC227583
0.8286	Intermediate Similarity	NPC12103
0.8273	Intermediate Similarity	NPC476594
0.8273	Intermediate Similarity	NPC94272
0.8273	Intermediate Similarity	NPC470432
0.8273	Intermediate Similarity	NPC14704
0.8273	Intermediate Similarity	NPC305423
0.8273	Intermediate Similarity	NPC230507
0.8273	Intermediate Similarity	NPC283829
0.8273	Intermediate Similarity	NPC113044
0.8273	Intermediate Similarity	NPC161676
0.8261	Intermediate Similarity	NPC203862
0.8257	Intermediate Similarity	NPC273879
0.8257	Intermediate Similarity	NPC475521
0.8257	Intermediate Similarity	NPC165033
0.8257	Intermediate Similarity	NPC152966
0.8252	Intermediate Similarity	NPC41554
0.8252	Intermediate Similarity	NPC97404
0.8246	Intermediate Similarity	NPC11548
0.8246	Intermediate Similarity	NPC167183
0.8246	Intermediate Similarity	NPC477810
0.8246	Intermediate Similarity	NPC32707
0.8241	Intermediate Similarity	NPC288694
0.8241	Intermediate Similarity	NPC22634
0.8241	Intermediate Similarity	NPC312553
0.8241	Intermediate Similarity	NPC159036
0.823	Intermediate Similarity	NPC472716
0.823	Intermediate Similarity	NPC254255
0.8224	Intermediate Similarity	NPC282669
0.8208	Intermediate Similarity	NPC76486
0.8208	Intermediate Similarity	NPC261807
0.8198	Intermediate Similarity	NPC295980
0.8198	Intermediate Similarity	NPC98696
0.819	Intermediate Similarity	NPC472080
0.819	Intermediate Similarity	NPC475403
0.819	Intermediate Similarity	NPC8774
0.819	Intermediate Similarity	NPC160888
0.8182	Intermediate Similarity	NPC194842
0.8182	Intermediate Similarity	NPC127801
0.8182	Intermediate Similarity	NPC152584
0.8182	Intermediate Similarity	NPC470767
0.8182	Intermediate Similarity	NPC208477
0.8182	Intermediate Similarity	NPC208594
0.8182	Intermediate Similarity	NPC69737
0.8182	Intermediate Similarity	NPC470763
0.8182	Intermediate Similarity	NPC160816
0.8182	Intermediate Similarity	NPC473199
0.8182	Intermediate Similarity	NPC269627
0.8174	Intermediate Similarity	NPC477030
0.8174	Intermediate Similarity	NPC477029
0.8174	Intermediate Similarity	NPC148965
0.8165	Intermediate Similarity	NPC471887
0.8165	Intermediate Similarity	NPC471886
0.8165	Intermediate Similarity	NPC471888
0.8165	Intermediate Similarity	NPC471885
0.8165	Intermediate Similarity	NPC162354
0.8165	Intermediate Similarity	NPC16573
0.8158	Intermediate Similarity	NPC79900
0.8158	Intermediate Similarity	NPC469347
0.8158	Intermediate Similarity	NPC144068
0.8158	Intermediate Similarity	NPC476693

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 NPC477050 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1839
0.2-0.3	4186
0.3-0.4	1950
0.4-0.5	543
0.5-0.6	236
0.6-0.7	165
0.7-0.8	25
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
0.8034	Intermediate Similarity	NPD7328	Approved
0.8034	Intermediate Similarity	NPD7327	Approved
0.7983	Intermediate Similarity	NPD8380	Approved
0.7983	Intermediate Similarity	NPD8379	Approved
0.7983	Intermediate Similarity	NPD8335	Approved
0.7983	Intermediate Similarity	NPD8378	Approved
0.7983	Intermediate Similarity	NPD8296	Approved
0.7983	Intermediate Similarity	NPD8033	Approved
0.7966	Intermediate Similarity	NPD7516	Approved
0.7899	Intermediate Similarity	NPD8294	Approved
0.7899	Intermediate Similarity	NPD8377	Approved
0.7833	Intermediate Similarity	NPD7503	Approved
0.7478	Intermediate Similarity	NPD6412	Phase 2
0.744	Intermediate Similarity	NPD7507	Approved
0.7402	Intermediate Similarity	NPD7319	Approved
0.7358	Intermediate Similarity	NPD7524	Approved
0.7317	Intermediate Similarity	NPD6054	Approved
0.7238	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6370	Approved
0.7196	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7736	Approved
0.7177	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD6695	Phase 3
0.712	Intermediate Similarity	NPD6015	Approved
0.712	Intermediate Similarity	NPD6016	Approved
0.7107	Intermediate Similarity	NPD8133	Approved
0.7087	Intermediate Similarity	NPD7492	Approved
0.7063	Intermediate Similarity	NPD5988	Approved
0.704	Intermediate Similarity	NPD6319	Approved
0.7037	Intermediate Similarity	NPD7750	Discontinued
0.7031	Intermediate Similarity	NPD6616	Approved
0.7027	Intermediate Similarity	NPD8171	Discontinued
0.7025	Intermediate Similarity	NPD6882	Approved
0.7025	Intermediate Similarity	NPD8297	Approved
0.7019	Intermediate Similarity	NPD7525	Registered
0.6977	Remote Similarity	NPD7078	Approved
0.6977	Remote Similarity	NPD8293	Discontinued
0.6957	Remote Similarity	NPD7639	Approved
0.6957	Remote Similarity	NPD7640	Approved
0.6935	Remote Similarity	NPD7115	Discovery
0.6935	Remote Similarity	NPD6009	Approved
0.6917	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7638	Approved
0.6857	Remote Similarity	NPD6930	Phase 2
0.6857	Remote Similarity	NPD7514	Phase 3
0.6857	Remote Similarity	NPD6931	Approved
0.6842	Remote Similarity	NPD8449	Approved
0.6833	Remote Similarity	NPD6686	Approved
0.6829	Remote Similarity	NPD4632	Approved
0.6796	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8450	Suspended
0.6762	Remote Similarity	NPD6929	Approved
0.6752	Remote Similarity	NPD4159	Approved
0.6744	Remote Similarity	NPD6067	Discontinued
0.6721	Remote Similarity	NPD4634	Approved
0.6719	Remote Similarity	NPD8517	Approved
0.6719	Remote Similarity	NPD8516	Approved
0.6719	Remote Similarity	NPD8515	Approved
0.6719	Remote Similarity	NPD8513	Phase 3
0.6699	Remote Similarity	NPD7339	Approved
0.6699	Remote Similarity	NPD6942	Approved
0.6698	Remote Similarity	NPD6928	Phase 2
0.6698	Remote Similarity	NPD7332	Phase 2
0.6695	Remote Similarity	NPD5211	Phase 2
0.6694	Remote Similarity	NPD6899	Approved
0.6694	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6373	Approved
0.6639	Remote Similarity	NPD6372	Approved
0.6637	Remote Similarity	NPD7637	Suspended
0.6637	Remote Similarity	NPD7087	Discontinued
0.6636	Remote Similarity	NPD6902	Approved
0.6615	Remote Similarity	NPD8328	Phase 3
0.6612	Remote Similarity	NPD5697	Approved
0.661	Remote Similarity	NPD5344	Discontinued
0.6604	Remote Similarity	NPD7645	Phase 2
0.6602	Remote Similarity	NPD4785	Approved
0.6602	Remote Similarity	NPD4784	Approved
0.6585	Remote Similarity	NPD7290	Approved
0.6585	Remote Similarity	NPD7102	Approved
0.6585	Remote Similarity	NPD6883	Approved
0.6583	Remote Similarity	NPD5141	Approved
0.6571	Remote Similarity	NPD5776	Phase 2
0.6571	Remote Similarity	NPD6925	Approved
0.6571	Remote Similarity	NPD6932	Approved
0.6557	Remote Similarity	NPD7320	Approved
0.6545	Remote Similarity	NPD6893	Approved
0.6532	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6847	Approved
0.6532	Remote Similarity	NPD6869	Approved
0.6532	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD4696	Approved
0.6525	Remote Similarity	NPD5285	Approved
0.6525	Remote Similarity	NPD5286	Approved
0.6504	Remote Similarity	NPD6013	Approved
0.6504	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6014	Approved
0.6504	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD7604	Phase 2
0.6476	Remote Similarity	NPD6933	Approved
0.6475	Remote Similarity	NPD5701	Approved
0.6462	Remote Similarity	NPD5983	Phase 2
0.646	Remote Similarity	NPD6051	Approved
0.6458	Remote Similarity	NPD7625	Phase 1
0.6446	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4225	Approved
0.6435	Remote Similarity	NPD4202	Approved
0.6435	Remote Similarity	NPD6399	Phase 3
0.6423	Remote Similarity	NPD6011	Approved
0.6417	Remote Similarity	NPD5226	Approved
0.6417	Remote Similarity	NPD4633	Approved
0.6417	Remote Similarity	NPD5224	Approved
0.6417	Remote Similarity	NPD7632	Discontinued
0.6417	Remote Similarity	NPD5225	Approved
0.6408	Remote Similarity	NPD4243	Approved
0.64	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6008	Approved
0.6391	Remote Similarity	NPD6336	Discontinued
0.6389	Remote Similarity	NPD4748	Discontinued
0.6387	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6356	Remote Similarity	NPD6084	Phase 2
0.6356	Remote Similarity	NPD6083	Phase 2
0.6343	Remote Similarity	NPD8074	Phase 3
0.6333	Remote Similarity	NPD5223	Approved
0.633	Remote Similarity	NPD6898	Phase 1
0.6324	Remote Similarity	NPD5956	Approved
0.632	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4786	Approved
0.6303	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6683	Phase 2
0.629	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4730	Approved
0.629	Remote Similarity	NPD4729	Approved
0.6286	Remote Similarity	NPD6926	Approved
0.6286	Remote Similarity	NPD6924	Approved
0.6261	Remote Similarity	NPD3168	Discontinued
0.6261	Remote Similarity	NPD7136	Phase 2
0.626	Remote Similarity	NPD4768	Approved
0.626	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD6648	Approved
0.623	Remote Similarity	NPD4754	Approved
0.6226	Remote Similarity	NPD8264	Approved
0.622	Remote Similarity	NPD6053	Discontinued
0.6207	Remote Similarity	NPD6079	Approved
0.6207	Remote Similarity	NPD8035	Phase 2
0.6207	Remote Similarity	NPD8034	Phase 2
0.6204	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5247	Approved
0.619	Remote Similarity	NPD5248	Approved
0.619	Remote Similarity	NPD5249	Phase 3
0.619	Remote Similarity	NPD5250	Approved
0.6183	Remote Similarity	NPD7101	Approved
0.6183	Remote Similarity	NPD7100	Approved
0.6174	Remote Similarity	NPD4753	Phase 2
0.6174	Remote Similarity	NPD5328	Approved
0.6161	Remote Similarity	NPD3668	Phase 3
0.6154	Remote Similarity	NPD6317	Approved
0.6147	Remote Similarity	NPD4195	Approved
0.6136	Remote Similarity	NPD7741	Discontinued
0.6129	Remote Similarity	NPD6640	Phase 3
0.6126	Remote Similarity	NPD3667	Approved
0.6107	Remote Similarity	NPD6335	Approved
0.6102	Remote Similarity	NPD7748	Approved
0.6095	Remote Similarity	NPD7151	Approved
0.6095	Remote Similarity	NPD7152	Approved
0.6095	Remote Similarity	NPD7150	Approved
0.6091	Remote Similarity	NPD7509	Discontinued
0.6083	Remote Similarity	NPD7902	Approved
0.608	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6274	Approved
0.6075	Remote Similarity	NPD5275	Approved
0.6075	Remote Similarity	NPD4190	Phase 3
0.6063	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD5135	Approved
0.6058	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3618	Phase 1
0.605	Remote Similarity	NPD5210	Approved
0.605	Remote Similarity	NPD4629	Approved
0.605	Remote Similarity	NPD7991	Discontinued
0.605	Remote Similarity	NPD5695	Phase 3
0.6033	Remote Similarity	NPD5696	Approved
0.6032	Remote Similarity	NPD5128	Approved
0.6018	Remote Similarity	NPD3133	Approved
0.6018	Remote Similarity	NPD3666	Approved
0.6018	Remote Similarity	NPD3665	Phase 1
0.6016	Remote Similarity	NPD5217	Approved
0.6016	Remote Similarity	NPD5216	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