NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1239.51
Volume:	1152.895
LogP:	0.569
LogD:	0.075
LogS:	-3.378
# Rotatable Bonds:	19
TPSA:	421.47
# H-Bond Aceptor:	28
# H-Bond Donor:	10
# Rings:	9
# Heavy Atoms:	29

MedChem Properties

QED Drug-Likeness Score:	0.023
Synthetic Accessibility Score:	7.875
Fsp3:	0.911
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:	-5.902
MDCK Permeability:	0.0005183891043998301
Pgp-inhibitor:	0.51
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.845
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	52.04914093017578%
Volume Distribution (VD):	0.151
Pgp-substrate:	23.475147247314453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.478
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	0.754
Half-life (T1/2):	0.471

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.512
AMES Toxicity:	0.136
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.168
Carcinogencity:	0.584
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC477232

Natural Product ID:	NPC477232
*Common Name:**	Fuscocineroside A
IUPAC Name:	sodium;[(3R,4R,5R,6S)-6-[[(1S,2S,5S,6R,9R,10S,13S,16S,18R)-6-(4-acetyloxy-4-methylpentanoyl)-10-hydroxy-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-11-en-16-yl]oxy]-5-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxyoxan-3-yl] sulfate
Synonyms:
Standard InCHIKey:	CVQMQSOXIPMRQC-GIOVIYMQSA-M
Standard InCHI:	InChI=1S/C56H88O28S.Na/c1-23-42(79-48-41(68)44(36(63)28(21-58)77-48)80-47-40(67)43(73-10)35(62)27(20-57)76-47)38(65)39(66)46(75-23)81-45-37(64)29(84-85(70,71)72)22-74-49(45)78-34-15-17-53(7)26-19-33(61)56-31(13-18-54(56,8)25(26)11-12-30(53)52(34,5)6)55(9,83-50(56)69)32(60)14-16-51(3,4)82-24(2)59;/h19,23,25,27-31,33-49,57-58,61-68H,11-18,20-22H2,1-10H3,(H,70,71,72);/q;+1/p-1/t23-,25-,27-,28-,29-,30+,31-,33+,34+,35-,36-,37+,38-,39-,40-,41-,42-,43+,44+,45-,46+,47+,48+,49+,53-,54+,55-,56-;/m1./s1
SMILES:	C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](CO[C@H]2O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@H]5C4=C[C@@H]([C@]67[C@]5(CC[C@@H]6[C@](OC7=O)(C)C(=O)CCC(C)(C)OC(=O)C)C)O)C)OS(=O)(=O)[O-])O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)OC)O)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559160
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO16258	Holothuria fuscocinerea	Species	Holothuriidae	Eukaryota	n.a.	collected at a depth of 2-30 m by a fishery bottom trawler from offshore waters of Leizhou Bay (Zhanjiang, Guangdong Province) in the South China Sea	2004-NOV	PMID[17067169]
NPO16258	Holothuria fuscocinerea	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6210	nM	PMID[17067169]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	5580	nM	PMID[17067169]

☑ 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 NPC477232 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	337
0.1-0.2	2099
0.2-0.3	5970
0.3-0.4	11120
0.4-0.5	10454
0.5-0.6	6837
0.6-0.7	3614
0.7-0.8	1758
0.8-0.85	441
0.85-0.9	56
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477233
0.9528	High Similarity	NPC478069
0.9375	High Similarity	NPC477234
0.9365	High Similarity	NPC477235
0.9231	High Similarity	NPC477236
0.8898	High Similarity	NPC476674
0.8828	High Similarity	NPC476673
0.875	High Similarity	NPC130229
0.8692	High Similarity	NPC470476
0.8692	High Similarity	NPC470475
0.8682	High Similarity	NPC469947
0.8682	High Similarity	NPC470218
0.8682	High Similarity	NPC104427
0.8682	High Similarity	NPC181066
0.8672	High Similarity	NPC281148
0.8672	High Similarity	NPC235405
0.8672	High Similarity	NPC30735
0.8661	High Similarity	NPC476672
0.8657	High Similarity	NPC251998
0.8615	High Similarity	NPC292290
0.8605	High Similarity	NPC470477
0.8594	High Similarity	NPC187290
0.8594	High Similarity	NPC236870
0.8594	High Similarity	NPC107966
0.8594	High Similarity	NPC80986
0.8594	High Similarity	NPC21691
0.8594	High Similarity	NPC10607
0.8594	High Similarity	NPC249848
0.8594	High Similarity	NPC40775
0.8594	High Similarity	NPC162574
0.8594	High Similarity	NPC4749
0.8594	High Similarity	NPC475591
0.8594	High Similarity	NPC235438
0.8593	High Similarity	NPC295885
0.8593	High Similarity	NPC140045
0.8582	High Similarity	NPC262813
0.8571	High Similarity	NPC475487
0.8538	High Similarity	NPC285091
0.8527	High Similarity	NPC283417
0.8527	High Similarity	NPC302543
0.8527	High Similarity	NPC257211
0.8527	High Similarity	NPC258617
0.8527	High Similarity	NPC200049
0.8519	High Similarity	NPC141215
0.8519	High Similarity	NPC471089
0.8519	High Similarity	NPC190065
0.8516	High Similarity	NPC114484
0.8516	High Similarity	NPC301449
0.8516	High Similarity	NPC22956
0.8516	High Similarity	NPC64715
0.8516	High Similarity	NPC470478
0.8516	High Similarity	NPC62725
0.8516	High Similarity	NPC222580
0.8516	High Similarity	NPC159309
0.8516	High Similarity	NPC11242
0.8516	High Similarity	NPC171544
0.8516	High Similarity	NPC31838
0.8516	High Similarity	NPC302887
0.8516	High Similarity	NPC86222
0.8516	High Similarity	NPC223301
0.8516	High Similarity	NPC297263
0.8516	High Similarity	NPC187618
0.8516	High Similarity	NPC104372
0.8496	Intermediate Similarity	NPC473519
0.8496	Intermediate Similarity	NPC473805
0.8473	Intermediate Similarity	NPC2757
0.8462	Intermediate Similarity	NPC30188
0.8462	Intermediate Similarity	NPC33068
0.8462	Intermediate Similarity	NPC247315
0.8462	Intermediate Similarity	NPC160452
0.8462	Intermediate Similarity	NPC471963
0.8462	Intermediate Similarity	NPC23275
0.8462	Intermediate Similarity	NPC471962
0.8462	Intermediate Similarity	NPC177820
0.8456	Intermediate Similarity	NPC596
0.845	Intermediate Similarity	NPC313110
0.845	Intermediate Similarity	NPC131824
0.845	Intermediate Similarity	NPC213952
0.845	Intermediate Similarity	NPC131469
0.8438	Intermediate Similarity	NPC129393
0.8438	Intermediate Similarity	NPC236657
0.8438	Intermediate Similarity	NPC118440
0.8438	Intermediate Similarity	NPC476849
0.8433	Intermediate Similarity	NPC102015
0.8397	Intermediate Similarity	NPC273962
0.8397	Intermediate Similarity	NPC475368
0.8397	Intermediate Similarity	NPC284449
0.8394	Intermediate Similarity	NPC79250
0.8394	Intermediate Similarity	NPC290746
0.8385	Intermediate Similarity	NPC160084
0.8385	Intermediate Similarity	NPC262199
0.8385	Intermediate Similarity	NPC478066
0.8385	Intermediate Similarity	NPC471964
0.8385	Intermediate Similarity	NPC44716
0.8385	Intermediate Similarity	NPC14617
0.8385	Intermediate Similarity	NPC2370
0.8385	Intermediate Similarity	NPC471961
0.8385	Intermediate Similarity	NPC202666
0.8385	Intermediate Similarity	NPC228701
0.8372	Intermediate Similarity	NPC476544
0.8372	Intermediate Similarity	NPC75417
0.8372	Intermediate Similarity	NPC182900
0.8372	Intermediate Similarity	NPC475182
0.8372	Intermediate Similarity	NPC476543
0.8372	Intermediate Similarity	NPC476545
0.8372	Intermediate Similarity	NPC249553
0.8372	Intermediate Similarity	NPC476675
0.8359	Intermediate Similarity	NPC475171
0.8359	Intermediate Similarity	NPC207738
0.8359	Intermediate Similarity	NPC157868
0.8359	Intermediate Similarity	NPC35405
0.8359	Intermediate Similarity	NPC51564
0.8359	Intermediate Similarity	NPC39211
0.8359	Intermediate Similarity	NPC469945
0.8359	Intermediate Similarity	NPC11551
0.8359	Intermediate Similarity	NPC25663
0.8359	Intermediate Similarity	NPC6377
0.8359	Intermediate Similarity	NPC214484
0.8359	Intermediate Similarity	NPC135849
0.8359	Intermediate Similarity	NPC192791
0.8359	Intermediate Similarity	NPC208381
0.8359	Intermediate Similarity	NPC114441
0.8359	Intermediate Similarity	NPC472949
0.8359	Intermediate Similarity	NPC309780
0.8359	Intermediate Similarity	NPC473884
0.8359	Intermediate Similarity	NPC180550
0.8358	Intermediate Similarity	NPC478154
0.8358	Intermediate Similarity	NPC476776
0.8346	Intermediate Similarity	NPC54614
0.8346	Intermediate Similarity	NPC309096
0.8346	Intermediate Similarity	NPC265841
0.8346	Intermediate Similarity	NPC47995
0.8333	Intermediate Similarity	NPC470780
0.8321	Intermediate Similarity	NPC473505
0.8321	Intermediate Similarity	NPC473474
0.8321	Intermediate Similarity	NPC248202
0.8308	Intermediate Similarity	NPC305771
0.8308	Intermediate Similarity	NPC471965
0.8308	Intermediate Similarity	NPC15918
0.8308	Intermediate Similarity	NPC169816
0.8308	Intermediate Similarity	NPC94072
0.8308	Intermediate Similarity	NPC156789
0.8296	Intermediate Similarity	NPC478151
0.8296	Intermediate Similarity	NPC476779
0.8295	Intermediate Similarity	NPC476670
0.8295	Intermediate Similarity	NPC267694
0.8295	Intermediate Similarity	NPC153673
0.8295	Intermediate Similarity	NPC473645
0.8295	Intermediate Similarity	NPC476991
0.8295	Intermediate Similarity	NPC144644
0.8295	Intermediate Similarity	NPC110385
0.8295	Intermediate Similarity	NPC472257
0.8295	Intermediate Similarity	NPC142151
0.8295	Intermediate Similarity	NPC37860
0.8284	Intermediate Similarity	NPC264566
0.8284	Intermediate Similarity	NPC478065
0.8284	Intermediate Similarity	NPC476775
0.8284	Intermediate Similarity	NPC134914
0.8284	Intermediate Similarity	NPC476774
0.8284	Intermediate Similarity	NPC262796
0.8284	Intermediate Similarity	NPC478064
0.8284	Intermediate Similarity	NPC271610
0.8284	Intermediate Similarity	NPC475167
0.8284	Intermediate Similarity	NPC173435
0.8284	Intermediate Similarity	NPC172374
0.8284	Intermediate Similarity	NPC476780
0.8284	Intermediate Similarity	NPC45346
0.8284	Intermediate Similarity	NPC329993
0.8284	Intermediate Similarity	NPC241008
0.8284	Intermediate Similarity	NPC476074
0.8284	Intermediate Similarity	NPC25998
0.8284	Intermediate Similarity	NPC478155
0.8284	Intermediate Similarity	NPC301639
0.8284	Intermediate Similarity	NPC475377
0.8281	Intermediate Similarity	NPC286347
0.8281	Intermediate Similarity	NPC105800
0.8281	Intermediate Similarity	NPC109588
0.8281	Intermediate Similarity	NPC232237
0.8271	Intermediate Similarity	NPC295220
0.8271	Intermediate Similarity	NPC475636
0.8268	Intermediate Similarity	NPC146652
0.8268	Intermediate Similarity	NPC279638
0.8258	Intermediate Similarity	NPC47113
0.8258	Intermediate Similarity	NPC87662
0.8258	Intermediate Similarity	NPC174367
0.8248	Intermediate Similarity	NPC329675
0.8244	Intermediate Similarity	NPC256983
0.8235	Intermediate Similarity	NPC476777
0.8235	Intermediate Similarity	NPC476778
0.8231	Intermediate Similarity	NPC51099
0.8231	Intermediate Similarity	NPC293031
0.8231	Intermediate Similarity	NPC68767
0.8231	Intermediate Similarity	NPC275225
0.8231	Intermediate Similarity	NPC31193
0.8231	Intermediate Similarity	NPC242840
0.8222	Intermediate Similarity	NPC233223
0.8222	Intermediate Similarity	NPC478150
0.8222	Intermediate Similarity	NPC475444
0.8222	Intermediate Similarity	NPC277212
0.8222	Intermediate Similarity	NPC183816

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 NPC477232 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	2260
0.2-0.3	4073
0.3-0.4	1606
0.4-0.5	518
0.5-0.6	249
0.6-0.7	106
0.7-0.8	33
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8385	Intermediate Similarity	NPD8328	Phase 3
0.8134	Intermediate Similarity	NPD7736	Approved
0.8062	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD8293	Discontinued
0.7955	Intermediate Similarity	NPD8517	Approved
0.7955	Intermediate Similarity	NPD8515	Approved
0.7955	Intermediate Similarity	NPD8516	Approved
0.7895	Intermediate Similarity	NPD6370	Approved
0.782	Intermediate Similarity	NPD8513	Phase 3
0.781	Intermediate Similarity	NPD7319	Approved
0.7778	Intermediate Similarity	NPD7492	Approved
0.7744	Intermediate Similarity	NPD6059	Approved
0.7744	Intermediate Similarity	NPD6054	Approved
0.7721	Intermediate Similarity	NPD6616	Approved
0.7721	Intermediate Similarity	NPD7507	Approved
0.7692	Intermediate Similarity	NPD8133	Approved
0.7664	Intermediate Similarity	NPD7078	Approved
0.7612	Intermediate Similarity	NPD8377	Approved
0.7612	Intermediate Similarity	NPD8294	Approved
0.7556	Intermediate Similarity	NPD8296	Approved
0.7556	Intermediate Similarity	NPD8380	Approved
0.7556	Intermediate Similarity	NPD8335	Approved
0.7556	Intermediate Similarity	NPD8379	Approved
0.7556	Intermediate Similarity	NPD8378	Approved
0.7556	Intermediate Similarity	NPD6015	Approved
0.7556	Intermediate Similarity	NPD6016	Approved
0.7519	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5988	Approved
0.7481	Intermediate Similarity	NPD6319	Approved
0.7426	Intermediate Similarity	NPD8033	Approved
0.7348	Intermediate Similarity	NPD8297	Approved
0.7348	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6009	Approved
0.7252	Intermediate Similarity	NPD6372	Approved
0.7252	Intermediate Similarity	NPD6373	Approved
0.7234	Intermediate Similarity	NPD6033	Approved
0.7231	Intermediate Similarity	NPD6412	Phase 2
0.7209	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7328	Approved
0.7206	Intermediate Similarity	NPD7327	Approved
0.7176	Intermediate Similarity	NPD7320	Approved
0.7154	Intermediate Similarity	NPD7128	Approved
0.7154	Intermediate Similarity	NPD6402	Approved
0.7154	Intermediate Similarity	NPD5739	Approved
0.7154	Intermediate Similarity	NPD6675	Approved
0.7153	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD6650	Approved
0.7143	Intermediate Similarity	NPD6649	Approved
0.7132	Intermediate Similarity	NPD7115	Discovery
0.705	Intermediate Similarity	NPD7503	Approved
0.7045	Intermediate Similarity	NPD6881	Approved
0.7045	Intermediate Similarity	NPD6686	Approved
0.7045	Intermediate Similarity	NPD6899	Approved
0.7045	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4632	Approved
0.7015	Intermediate Similarity	NPD8130	Phase 1
0.697	Remote Similarity	NPD5701	Approved
0.697	Remote Similarity	NPD5697	Approved
0.694	Remote Similarity	NPD7102	Approved
0.694	Remote Similarity	NPD7290	Approved
0.694	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD8074	Phase 3
0.6889	Remote Similarity	NPD6869	Approved
0.6889	Remote Similarity	NPD6847	Approved
0.6889	Remote Similarity	NPD6617	Approved
0.6889	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6013	Approved
0.6866	Remote Similarity	NPD6014	Approved
0.6866	Remote Similarity	NPD6012	Approved
0.6831	Remote Similarity	NPD7604	Phase 2
0.6815	Remote Similarity	NPD4634	Approved
0.6809	Remote Similarity	NPD5983	Phase 2
0.6791	Remote Similarity	NPD6011	Approved
0.6767	Remote Similarity	NPD6008	Approved
0.6736	Remote Similarity	NPD6336	Discontinued
0.6713	Remote Similarity	NPD6067	Discontinued
0.6692	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6615	Remote Similarity	NPD6083	Phase 2
0.6615	Remote Similarity	NPD6084	Phase 2
0.6615	Remote Similarity	NPD4755	Approved
0.6573	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6921	Approved
0.6571	Remote Similarity	NPD6274	Approved
0.6567	Remote Similarity	NPD5141	Approved
0.6562	Remote Similarity	NPD6399	Phase 3
0.6554	Remote Similarity	NPD5956	Approved
0.655	Remote Similarity	NPD7799	Discontinued
0.6549	Remote Similarity	NPD7100	Approved
0.6549	Remote Similarity	NPD7101	Approved
0.6531	Remote Similarity	NPD8337	Approved
0.6531	Remote Similarity	NPD8336	Approved
0.6525	Remote Similarity	NPD6317	Approved
0.6515	Remote Similarity	NPD7639	Approved
0.6515	Remote Similarity	NPD5286	Approved
0.6515	Remote Similarity	NPD4700	Approved
0.6515	Remote Similarity	NPD4696	Approved
0.6515	Remote Similarity	NPD7640	Approved
0.6515	Remote Similarity	NPD5285	Approved
0.6489	Remote Similarity	NPD7902	Approved
0.6479	Remote Similarity	NPD6335	Approved
0.6458	Remote Similarity	NPD6909	Approved
0.6458	Remote Similarity	NPD6908	Approved
0.6439	Remote Similarity	NPD4225	Approved
0.6439	Remote Similarity	NPD7638	Approved
0.6434	Remote Similarity	NPD8171	Discontinued
0.6424	Remote Similarity	NPD8450	Suspended
0.6418	Remote Similarity	NPD5226	Approved
0.6418	Remote Similarity	NPD4633	Approved
0.6418	Remote Similarity	NPD5224	Approved
0.6418	Remote Similarity	NPD5225	Approved
0.6412	Remote Similarity	NPD4697	Phase 3
0.64	Remote Similarity	NPD7260	Phase 2
0.6397	Remote Similarity	NPD4767	Approved
0.6397	Remote Similarity	NPD4768	Approved
0.6385	Remote Similarity	NPD7748	Approved
0.6377	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.637	Remote Similarity	NPD5174	Approved
0.637	Remote Similarity	NPD5175	Approved
0.637	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD6313	Approved
0.6364	Remote Similarity	NPD6314	Approved
0.6358	Remote Similarity	NPD8338	Approved
0.6358	Remote Similarity	NPD6845	Suspended
0.6358	Remote Similarity	NPD8449	Approved
0.6357	Remote Similarity	NPD8035	Phase 2
0.6357	Remote Similarity	NPD8034	Phase 2
0.635	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5223	Approved
0.6338	Remote Similarity	NPD6868	Approved
0.6336	Remote Similarity	NPD5695	Phase 3
0.6331	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5328	Approved
0.6304	Remote Similarity	NPD4729	Approved
0.6304	Remote Similarity	NPD4730	Approved
0.6299	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5221	Approved
0.6288	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5222	Approved
0.626	Remote Similarity	NPD7900	Approved
0.626	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6672	Approved
0.625	Remote Similarity	NPD7625	Phase 1
0.6241	Remote Similarity	NPD5173	Approved
0.6241	Remote Similarity	NPD6053	Discontinued
0.6234	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7983	Approved
0.6231	Remote Similarity	NPD6079	Approved
0.6231	Remote Similarity	NPD7515	Phase 2
0.6216	Remote Similarity	NPD8341	Approved
0.6216	Remote Similarity	NPD8340	Approved
0.6216	Remote Similarity	NPD8342	Approved
0.6216	Remote Similarity	NPD8299	Approved
0.6214	Remote Similarity	NPD5250	Approved
0.6214	Remote Similarity	NPD5248	Approved
0.6214	Remote Similarity	NPD5249	Phase 3
0.6214	Remote Similarity	NPD5251	Approved
0.6214	Remote Similarity	NPD5247	Approved
0.6212	Remote Similarity	NPD5210	Approved
0.6212	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD4629	Approved
0.6204	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8080	Discontinued
0.6187	Remote Similarity	NPD5128	Approved
0.6183	Remote Similarity	NPD5779	Approved
0.6183	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD6333	Approved
0.6154	Remote Similarity	NPD6334	Approved
0.6133	Remote Similarity	NPD8448	Approved
0.6122	Remote Similarity	NPD8444	Approved
0.6118	Remote Similarity	NPD8390	Approved
0.6118	Remote Similarity	NPD8392	Approved
0.6118	Remote Similarity	NPD8391	Approved
0.6115	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD7637	Suspended
0.6107	Remote Similarity	NPD6411	Approved
0.6103	Remote Similarity	NPD1700	Approved
0.6099	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD6371	Approved
0.6099	Remote Similarity	NPD5135	Approved
0.6094	Remote Similarity	NPD6098	Approved
0.6094	Remote Similarity	NPD3618	Phase 1
0.6077	Remote Similarity	NPD4753	Phase 2
0.6077	Remote Similarity	NPD6080	Approved
0.6077	Remote Similarity	NPD6904	Approved
0.6077	Remote Similarity	NPD6673	Approved
0.6067	Remote Similarity	NPD8451	Approved
0.6065	Remote Similarity	NPD8415	Approved
0.6063	Remote Similarity	NPD4786	Approved
0.6061	Remote Similarity	NPD4202	Approved
0.6058	Remote Similarity	NPD7632	Discontinued
0.6056	Remote Similarity	NPD5217	Approved
0.6056	Remote Similarity	NPD5216	Approved
0.6056	Remote Similarity	NPD5215	Approved
0.6016	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD5282	Discontinued

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