NPASS Compound

Structure

NPC474829 OpenBabel07101718182D 26 26 0 0 1 0 0 0 0 0999 V2000 6.9927 -4.1547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7633 -2.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5401 -3.5877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6654 -1.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8948 -3.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2770 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4575 -2.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9223 -0.8601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1517 -2.8675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2281 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8459 -3.2276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0691 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -1.5084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3811 -4.8749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 -3.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2006 -3.1765 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.9712 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5890 -3.8967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1180 -2.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1243 -5.5440 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.0753 -5.2350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9164 -6.5222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2832 -4.2569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8185 -5.9041 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.8090 -3.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 17 1 0 0 0 0 8 18 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 26 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 M CHG 1 25 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	359.22
Volume:	398.536
LogP:	3.331
LogD:	2.387
LogS:	-3.893
# Rotatable Bonds:	13
TPSA:	70.34
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	4.134
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.704
MDCK Permeability:	3.207149711670354e-05
Pgp-inhibitor:	0.36
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	97.15921783447266%
Volume Distribution (VD):	1.097
Pgp-substrate:	2.0099949836730957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.48
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.829
CYP2C19-substrate:	0.214
CYP2C9-inhibitor:	0.928
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.334
CYP2D6-substrate:	0.733
CYP3A4-inhibitor:	0.723
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	3.262
Half-life (T1/2):	0.732

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.672
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.603
Skin Sensitization:	0.412
Carcinogencity:	0.728
Eye Corrosion:	0.166
Eye Irritation:	0.584
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC474829

Natural Product ID:	NPC474829
*Common Name:**	Sarcotin I
IUPAC Name:	sodium;(4Z,8R,9E,11E)-15-(furan-3-yl)-2-hydroxy-4,8,12-trimethylpentadeca-4,9,11-trienoate
Synonyms:	Sarcotin I
Standard InCHIKey:	UNRMHKZMQXKKAP-KGEDCXCLSA-M
Standard InCHI:	InChI=1S/C22H32O4.Na/c1-17(9-5-11-19(3)15-21(23)22(24)25)7-4-8-18(2)10-6-12-20-13-14-26-16-20;/h4,7-8,11,13-14,16-17,21,23H,5-6,9-10,12,15H2,1-3H3,(H,24,25);/q;+1/p-1/b7-4+,18-8+,19-11-;/t17-,21?;/m0./s1
SMILES:	CC(CCC=C(C)CC(C(=O)[O-])O)C=CC=C(C)CCCC1=COC=C1.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484249
PubChem CID:	44575988
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
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678655]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350153]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341287]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	24.8	ug ml-1	PMID[554464]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	23.3	ug ml-1	PMID[554464]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	25.7	ug ml-1	PMID[554464]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	25.9	ug ml-1	PMID[554464]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	23.7	ug ml-1	PMID[554464]

☑ 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 NPC474829 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	222
0.1-0.2	1085
0.2-0.3	3482
0.3-0.4	8911
0.4-0.5	11447
0.5-0.6	9919
0.6-0.7	6943
0.7-0.8	585
0.8-0.85	63
0.85-0.9	28
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9832	High Similarity	NPC474830
0.9421	High Similarity	NPC474260
0.9421	High Similarity	NPC329694
0.9421	High Similarity	NPC329922
0.9421	High Similarity	NPC81912
0.9187	High Similarity	NPC476016
0.918	High Similarity	NPC75557
0.918	High Similarity	NPC71274
0.9174	High Similarity	NPC475818
0.9153	High Similarity	NPC208906
0.9153	High Similarity	NPC144745
0.9113	High Similarity	NPC474279
0.9113	High Similarity	NPC474438
0.9032	High Similarity	NPC473355
0.9032	High Similarity	NPC471573
0.9032	High Similarity	NPC471554
0.9032	High Similarity	NPC471501
0.9024	High Similarity	NPC471559
0.9016	High Similarity	NPC476351
0.8934	High Similarity	NPC283284
0.8934	High Similarity	NPC289911
0.8934	High Similarity	NPC473379
0.8934	High Similarity	NPC471549
0.8926	High Similarity	NPC474817
0.8906	High Similarity	NPC474425
0.8906	High Similarity	NPC474407
0.8906	High Similarity	NPC474426
0.8898	High Similarity	NPC17681
0.8852	High Similarity	NPC474136
0.8843	High Similarity	NPC473969
0.8828	High Similarity	NPC97740
0.879	High Similarity	NPC243269
0.8729	High Similarity	NPC1811
0.8729	High Similarity	NPC26157
0.8702	High Similarity	NPC303217
0.8682	High Similarity	NPC45358
0.8678	High Similarity	NPC131801
0.8547	High Similarity	NPC471521
0.8547	High Similarity	NPC473356
0.8538	High Similarity	NPC473982
0.8507	High Similarity	NPC107571
0.8504	High Similarity	NPC46536
0.8504	High Similarity	NPC138139
0.8492	Intermediate Similarity	NPC118853
0.8487	Intermediate Similarity	NPC105249
0.848	Intermediate Similarity	NPC477967
0.8475	Intermediate Similarity	NPC177331
0.8462	Intermediate Similarity	NPC89133
0.8455	Intermediate Similarity	NPC21831
0.8455	Intermediate Similarity	NPC187547
0.8438	Intermediate Similarity	NPC83178
0.8438	Intermediate Similarity	NPC137570
0.84	Intermediate Similarity	NPC79557
0.84	Intermediate Similarity	NPC1848
0.8397	Intermediate Similarity	NPC471545
0.8397	Intermediate Similarity	NPC471544
0.8397	Intermediate Similarity	NPC473344
0.8397	Intermediate Similarity	NPC471817
0.8372	Intermediate Similarity	NPC207294
0.8372	Intermediate Similarity	NPC112706
0.8361	Intermediate Similarity	NPC28054
0.8358	Intermediate Similarity	NPC170604
0.8358	Intermediate Similarity	NPC215109
0.8358	Intermediate Similarity	NPC473268
0.8346	Intermediate Similarity	NPC188377
0.8346	Intermediate Similarity	NPC65735
0.8333	Intermediate Similarity	NPC263870
0.8333	Intermediate Similarity	NPC218838
0.8281	Intermediate Similarity	NPC179354
0.8268	Intermediate Similarity	NPC16922
0.824	Intermediate Similarity	NPC4898
0.8235	Intermediate Similarity	NPC90953
0.8217	Intermediate Similarity	NPC23086
0.8209	Intermediate Similarity	NPC476947
0.8209	Intermediate Similarity	NPC14650
0.8201	Intermediate Similarity	NPC137295
0.8182	Intermediate Similarity	NPC61788
0.816	Intermediate Similarity	NPC243704
0.8145	Intermediate Similarity	NPC45536
0.8134	Intermediate Similarity	NPC288209
0.8092	Intermediate Similarity	NPC26532
0.8088	Intermediate Similarity	NPC186626
0.808	Intermediate Similarity	NPC312525
0.808	Intermediate Similarity	NPC217180
0.808	Intermediate Similarity	NPC227660
0.8077	Intermediate Similarity	NPC74612
0.8074	Intermediate Similarity	NPC159786
0.8065	Intermediate Similarity	NPC205523
0.8065	Intermediate Similarity	NPC150895
0.8062	Intermediate Similarity	NPC477038
0.8062	Intermediate Similarity	NPC477965
0.806	Intermediate Similarity	NPC470740
0.8047	Intermediate Similarity	NPC317217
0.8045	Intermediate Similarity	NPC298190
0.8043	Intermediate Similarity	NPC473983
0.8043	Intermediate Similarity	NPC201370
0.803	Intermediate Similarity	NPC208389
0.8016	Intermediate Similarity	NPC254958
0.8016	Intermediate Similarity	NPC291619
0.8015	Intermediate Similarity	NPC246392
0.8015	Intermediate Similarity	NPC319140
0.8015	Intermediate Similarity	NPC95567
0.8	Intermediate Similarity	NPC106247
0.8	Intermediate Similarity	NPC474378
0.8	Intermediate Similarity	NPC474219
0.8	Intermediate Similarity	NPC254198
0.8	Intermediate Similarity	NPC147168
0.7971	Intermediate Similarity	NPC202260
0.7955	Intermediate Similarity	NPC329707
0.7943	Intermediate Similarity	NPC307346
0.7943	Intermediate Similarity	NPC267004
0.7943	Intermediate Similarity	NPC476944
0.7943	Intermediate Similarity	NPC261733
0.7943	Intermediate Similarity	NPC218712
0.7941	Intermediate Similarity	NPC92941
0.7929	Intermediate Similarity	NPC52412
0.7929	Intermediate Similarity	NPC121158
0.7923	Intermediate Similarity	NPC130275
0.7917	Intermediate Similarity	NPC125182
0.7917	Intermediate Similarity	NPC69647
0.7917	Intermediate Similarity	NPC234494
0.7914	Intermediate Similarity	NPC90296
0.791	Intermediate Similarity	NPC136340
0.7895	Intermediate Similarity	NPC223063
0.7895	Intermediate Similarity	NPC120836
0.7891	Intermediate Similarity	NPC281258
0.7883	Intermediate Similarity	NPC146872
0.7879	Intermediate Similarity	NPC290955
0.7877	Intermediate Similarity	NPC294511
0.7877	Intermediate Similarity	NPC44577
0.7877	Intermediate Similarity	NPC121615
0.7872	Intermediate Similarity	NPC243577
0.7872	Intermediate Similarity	NPC267632
0.7872	Intermediate Similarity	NPC476946
0.7862	Intermediate Similarity	NPC470997
0.7857	Intermediate Similarity	NPC474987
0.7857	Intermediate Similarity	NPC476014
0.7857	Intermediate Similarity	NPC476031
0.7847	Intermediate Similarity	NPC7388
0.7836	Intermediate Similarity	NPC21460
0.7832	Intermediate Similarity	NPC104924
0.7826	Intermediate Similarity	NPC470742
0.7826	Intermediate Similarity	NPC310830
0.782	Intermediate Similarity	NPC477040
0.782	Intermediate Similarity	NPC477123
0.782	Intermediate Similarity	NPC477966
0.782	Intermediate Similarity	NPC477039
0.7817	Intermediate Similarity	NPC251865
0.7786	Intermediate Similarity	NPC67003
0.7786	Intermediate Similarity	NPC148374
0.7786	Intermediate Similarity	NPC282973
0.7785	Intermediate Similarity	NPC45101
0.7778	Intermediate Similarity	NPC475092
0.7778	Intermediate Similarity	NPC255414
0.7778	Intermediate Similarity	NPC250228
0.7778	Intermediate Similarity	NPC11821
0.7778	Intermediate Similarity	NPC476938
0.7778	Intermediate Similarity	NPC476937
0.7778	Intermediate Similarity	NPC477645
0.7778	Intermediate Similarity	NPC216755
0.7778	Intermediate Similarity	NPC471174
0.777	Intermediate Similarity	NPC236532
0.777	Intermediate Similarity	NPC472376
0.777	Intermediate Similarity	NPC476943
0.777	Intermediate Similarity	NPC220094
0.777	Intermediate Similarity	NPC214541
0.777	Intermediate Similarity	NPC44675
0.7762	Intermediate Similarity	NPC5676
0.7762	Intermediate Similarity	NPC195920
0.7755	Intermediate Similarity	NPC33938
0.7755	Intermediate Similarity	NPC246164
0.7746	Intermediate Similarity	NPC80635
0.7744	Intermediate Similarity	NPC474476
0.774	Intermediate Similarity	NPC228842
0.7734	Intermediate Similarity	NPC293424
0.7733	Intermediate Similarity	NPC475967
0.7733	Intermediate Similarity	NPC472779
0.7727	Intermediate Similarity	NPC300098
0.7727	Intermediate Similarity	NPC473885
0.7727	Intermediate Similarity	NPC290193
0.7727	Intermediate Similarity	NPC471074
0.7724	Intermediate Similarity	NPC476942
0.7724	Intermediate Similarity	NPC61284
0.7724	Intermediate Similarity	NPC476941
0.7724	Intermediate Similarity	NPC113428
0.7721	Intermediate Similarity	NPC471995
0.7721	Intermediate Similarity	NPC196979
0.7721	Intermediate Similarity	NPC470976
0.7721	Intermediate Similarity	NPC470977
0.7718	Intermediate Similarity	NPC469485
0.7717	Intermediate Similarity	NPC76844
0.771	Intermediate Similarity	NPC272899
0.7708	Intermediate Similarity	NPC475864
0.7708	Intermediate Similarity	NPC346
0.7704	Intermediate Similarity	NPC476925
0.7703	Intermediate Similarity	NPC253201
0.7703	Intermediate Similarity	NPC237259
0.7703	Intermediate Similarity	NPC34421
0.7703	Intermediate Similarity	NPC98206
0.7703	Intermediate Similarity	NPC302054

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 NPC474829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	926
0.2-0.3	1984
0.3-0.4	2703
0.4-0.5	2028
0.5-0.6	1021
0.6-0.7	268
0.7-0.8	13
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
0.7714	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6355	Discontinued
0.7552	Intermediate Similarity	NPD4628	Phase 3
0.7518	Intermediate Similarity	NPD6798	Discontinued
0.7353	Intermediate Similarity	NPD5647	Approved
0.7338	Intermediate Similarity	NPD4062	Phase 3
0.7338	Intermediate Similarity	NPD6233	Phase 2
0.7313	Intermediate Similarity	NPD9717	Approved
0.7252	Intermediate Similarity	NPD9092	Discovery
0.7246	Intermediate Similarity	NPD6832	Phase 2
0.7203	Intermediate Similarity	NPD2799	Discontinued
0.7181	Intermediate Similarity	NPD6273	Approved
0.7162	Intermediate Similarity	NPD6799	Approved
0.7153	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD3887	Approved
0.7133	Intermediate Similarity	NPD5403	Approved
0.7123	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5401	Approved
0.7109	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5761	Phase 2
0.7078	Intermediate Similarity	NPD5760	Phase 2
0.7077	Intermediate Similarity	NPD1241	Discontinued
0.7063	Intermediate Similarity	NPD6653	Approved
0.7055	Intermediate Similarity	NPD5958	Discontinued
0.7055	Intermediate Similarity	NPD6764	Approved
0.7055	Intermediate Similarity	NPD6765	Approved
0.7048	Intermediate Similarity	NPD8434	Phase 2
0.7029	Intermediate Similarity	NPD1203	Approved
0.7029	Intermediate Similarity	NPD6362	Approved
0.7023	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2313	Discontinued
0.7021	Intermediate Similarity	NPD3268	Approved
0.7013	Intermediate Similarity	NPD6801	Discontinued
0.6993	Remote Similarity	NPD6599	Discontinued
0.6986	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6002	Phase 3
0.6986	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6004	Phase 3
0.6986	Remote Similarity	NPD6005	Phase 3
0.6985	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1019	Discontinued
0.6966	Remote Similarity	NPD4308	Phase 3
0.6954	Remote Similarity	NPD5049	Phase 3
0.6953	Remote Similarity	NPD2684	Approved
0.6943	Remote Similarity	NPD7075	Discontinued
0.694	Remote Similarity	NPD9545	Approved
0.694	Remote Similarity	NPD1894	Discontinued
0.6939	Remote Similarity	NPD4534	Discontinued
0.6934	Remote Similarity	NPD1608	Approved
0.6929	Remote Similarity	NPD3134	Approved
0.6928	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1551	Phase 2
0.6906	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2067	Discontinued
0.6886	Remote Similarity	NPD6785	Approved
0.6886	Remote Similarity	NPD6784	Approved
0.6875	Remote Similarity	NPD447	Suspended
0.6875	Remote Similarity	NPD1358	Approved
0.6871	Remote Similarity	NPD5762	Approved
0.6871	Remote Similarity	NPD2344	Approved
0.6871	Remote Similarity	NPD2353	Approved
0.6871	Remote Similarity	NPD5763	Approved
0.6871	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7843	Approved
0.6857	Remote Similarity	NPD2798	Approved
0.6849	Remote Similarity	NPD7033	Discontinued
0.6848	Remote Similarity	NPD6559	Discontinued
0.6846	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4110	Phase 3
0.6831	Remote Similarity	NPD7095	Approved
0.6815	Remote Similarity	NPD5402	Approved
0.6809	Remote Similarity	NPD9494	Approved
0.6806	Remote Similarity	NPD4060	Phase 1
0.6806	Remote Similarity	NPD4307	Phase 2
0.6803	Remote Similarity	NPD2239	Approved
0.6803	Remote Similarity	NPD2240	Approved
0.6803	Remote Similarity	NPD2935	Discontinued
0.6797	Remote Similarity	NPD920	Approved
0.6792	Remote Similarity	NPD919	Approved
0.6791	Remote Similarity	NPD9493	Approved
0.679	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3496	Discontinued
0.6786	Remote Similarity	NPD3266	Approved
0.6786	Remote Similarity	NPD3267	Approved
0.6783	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD411	Approved
0.6776	Remote Similarity	NPD4661	Approved
0.6776	Remote Similarity	NPD4662	Approved
0.6767	Remote Similarity	NPD2629	Approved
0.6759	Remote Similarity	NPD1933	Approved
0.6759	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2346	Discontinued
0.6757	Remote Similarity	NPD1471	Phase 3
0.6755	Remote Similarity	NPD7440	Discontinued
0.6755	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD290	Approved
0.6738	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7157	Approved
0.6715	Remote Similarity	NPD1778	Approved
0.6715	Remote Similarity	NPD17	Approved
0.6714	Remote Similarity	NPD1876	Approved
0.6692	Remote Similarity	NPD2182	Approved
0.6691	Remote Similarity	NPD1481	Phase 2
0.6691	Remote Similarity	NPD3972	Approved
0.6689	Remote Similarity	NPD2309	Approved
0.6689	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD987	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2614	Approved
0.6642	Remote Similarity	NPD5585	Approved
0.664	Remote Similarity	NPD9495	Approved
0.6624	Remote Similarity	NPD7411	Suspended
0.6624	Remote Similarity	NPD958	Approved
0.6623	Remote Similarity	NPD7003	Approved
0.6623	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3750	Approved
0.6619	Remote Similarity	NPD1535	Discovery
0.6617	Remote Similarity	NPD5535	Approved
0.6606	Remote Similarity	NPD2163	Approved
0.6604	Remote Similarity	NPD3817	Phase 2
0.6603	Remote Similarity	NPD7458	Discontinued
0.6601	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1549	Phase 2
0.66	Remote Similarity	NPD2424	Discontinued
0.66	Remote Similarity	NPD2897	Discontinued
0.6597	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1283	Approved
0.6577	Remote Similarity	NPD4476	Approved
0.6577	Remote Similarity	NPD4477	Approved
0.6577	Remote Similarity	NPD2796	Approved
0.6575	Remote Similarity	NPD4140	Approved
0.6575	Remote Similarity	NPD3142	Approved
0.6575	Remote Similarity	NPD3140	Approved
0.6573	Remote Similarity	NPD454	Approved
0.6562	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1243	Approved
0.6556	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7819	Suspended
0.6541	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4618	Approved
0.6531	Remote Similarity	NPD4340	Discontinued
0.6531	Remote Similarity	NPD4622	Approved
0.6525	Remote Similarity	NPD3685	Discontinued
0.6522	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6677	Suspended
0.6513	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1237	Approved
0.651	Remote Similarity	NPD3748	Approved
0.6503	Remote Similarity	NPD8127	Discontinued
0.65	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2649	Approved
0.6497	Remote Similarity	NPD2651	Approved
0.6479	Remote Similarity	NPD3225	Approved
0.6467	Remote Similarity	NPD6032	Approved
0.6467	Remote Similarity	NPD2438	Suspended
0.6467	Remote Similarity	NPD5712	Approved
0.6463	Remote Similarity	NPD6808	Phase 2
0.6463	Remote Similarity	NPD2979	Phase 3
0.6462	Remote Similarity	NPD9697	Approved
0.646	Remote Similarity	NPD7768	Phase 2
0.6457	Remote Similarity	NPD1238	Approved
0.6456	Remote Similarity	NPD4380	Phase 2
0.6443	Remote Similarity	NPD5688	Approved
0.6443	Remote Similarity	NPD5689	Approved
0.6438	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1048	Approved
0.6434	Remote Similarity	NPD6647	Phase 2
0.6433	Remote Similarity	NPD957	Approved
0.642	Remote Similarity	NPD3749	Approved
0.6419	Remote Similarity	NPD230	Phase 1
0.6419	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5124	Phase 1
0.6418	Remote Similarity	NPD969	Suspended
0.6408	Remote Similarity	NPD4359	Approved
0.6407	Remote Similarity	NPD3818	Discontinued
0.6403	Remote Similarity	NPD5691	Approved
0.6402	Remote Similarity	NPD1247	Approved
0.6395	Remote Similarity	NPD8032	Phase 2
0.6392	Remote Similarity	NPD3226	Approved
0.6391	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6166	Phase 2
0.6386	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD164	Approved
0.6383	Remote Similarity	NPD1281	Approved
0.6382	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD970	Clinical (unspecified phase)

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