NPASS Compound

Structure

NPC474279 OpenBabel07101718292D 30 31 0 0 1 0 0 0 0 0999 V2000 4.5007 0.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7420 -1.6800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4291 0.3938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3781 -1.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1187 -0.2341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5639 -0.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4826 -0.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4646 -1.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2052 -0.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3729 -1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4943 0.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9278 -0.8219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6503 -1.0030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4889 0.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1525 -1.2773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3962 -0.0531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6555 -1.2733 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2864 -0.7773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8413 -0.4152 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7601 1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4346 0.4984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8956 -0.6081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 3 20 1 0 0 0 0 4 25 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 18 2 0 0 0 0 11 21 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 25 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 21 2 0 0 0 0 17 29 1 0 0 0 0 19 2 1 6 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 24 27 2 0 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.26
Volume:	451.976
LogP:	4.727
LogD:	4.094
LogS:	-4.616
# Rotatable Bonds:	12
TPSA:	86.97
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.337
Synthetic Accessibility Score:	3.99
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.821
MDCK Permeability:	2.4220118575613014e-05
Pgp-inhibitor:	0.549
Pgp-substrate:	0.118
Human Intestinal Absorption (HIA):	0.102
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	95.84357452392578%
Volume Distribution (VD):	1.871
Pgp-substrate:	1.6777266263961792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.357
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.684
CYP2C19-substrate:	0.147
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.708
CYP3A4-inhibitor:	0.612
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	7.936
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.422
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.545
Skin Sensitization:	0.476
Carcinogencity:	0.687
Eye Corrosion:	0.003
Eye Irritation:	0.13
Respiratory Toxicity:	0.665

Download Data

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

Natural Product: NPC474279

Natural Product ID:	NPC474279
*Common Name:**	(12E,20Z,18S)-8-Hydroxyvariabilin
IUPAC Name:	(5Z)-5-[(E,2S)-13-(furan-3-yl)-10-hydroxy-2,6,10-trimethyltridec-6-enylidene]-4-hydroxy-3-methylfuran-2-one
Synonyms:	(12E,20Z,18S)-8-Hydroxyvariabilin
Standard InCHIKey:	QFBUNOKEKXMSCV-UYYPKTQPSA-N
Standard InCHI:	InChI=1S/C25H36O5/c1-18(8-5-9-19(2)16-22-23(26)20(3)24(27)30-22)10-6-13-25(4,28)14-7-11-21-12-15-29-17-21/h10,12,15-17,19,26,28H,5-9,11,13-14H2,1-4H3/b18-10+,22-16-/t19-,25?/m0/s1
SMILES:	CC1=C(C(=CC(C)CCCC(=CCCC(C)(CCCC2=COC=C2)O)C)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464651
PubChem CID:	54726845
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33253	Irciniidae	Family	Irciniidae	Eukaryota	n.a.	Australian	n.a.	PMID[20346682]

☑ 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
EC50	1
IC50	7
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4324	Individual Protein	Glycine receptor subunit alpha-2	Homo sapiens	Inhibition	=	87.0	%	PMID[494662]
NPT426	Individual Protein	Glycine receptor subunit alpha-1	Homo sapiens	EC50	=	1200.0	nM	PMID[494662]
NPT426	Individual Protein	Glycine receptor subunit alpha-1	Homo sapiens	Activity	=	215.0	%	PMID[494662]
NPT4641	Individual Protein	Glycine receptor subunit alpha-3	Homo sapiens	IC50	=	7000.0	nM	PMID[494662]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	7100.0	nM	PMID[494663]
NPT1210	Individual Protein	T-cell protein-tyrosine phosphatase	Homo sapiens	IC50	=	3700.0	nM	PMID[494663]
NPT287	Individual Protein	Leukocyte common antigen	Homo sapiens	IC50	=	9000.0	nM	PMID[494663]
NPT1211	Individual Protein	Dual specificity protein phosphatase 3	Homo sapiens	IC50	=	9400.0	nM	PMID[494663]
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	>	50000.0	nM	PMID[494663]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[494663]
NPT2	Others	Unspecified		Ratio IC50	=	2.0	n.a.	PMID[494663]

☑ 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 NPC474279 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	238
0.1-0.2	1121
0.2-0.3	3315
0.3-0.4	8165
0.4-0.5	11316
0.5-0.6	8919
0.6-0.7	8790
0.7-0.8	740
0.8-0.85	46
0.85-0.9	31
0.9-0.95	7
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474438
0.9752	High Similarity	NPC476016
0.975	High Similarity	NPC71274
0.975	High Similarity	NPC75557
0.9669	High Similarity	NPC474260
0.9669	High Similarity	NPC329694
0.9669	High Similarity	NPC81912
0.9669	High Similarity	NPC329922
0.9583	High Similarity	NPC476351
0.95	High Similarity	NPC289911
0.95	High Similarity	NPC283284
0.9421	High Similarity	NPC475818
0.9417	High Similarity	NPC474136
0.9274	High Similarity	NPC474830
0.9174	High Similarity	NPC474817
0.9113	High Similarity	NPC474829
0.9091	High Similarity	NPC473969
0.9083	High Similarity	NPC208906
0.9083	High Similarity	NPC144745
0.9062	High Similarity	NPC97740
0.9008	High Similarity	NPC170604
0.9008	High Similarity	NPC215109
0.8992	High Similarity	NPC474407
0.8992	High Similarity	NPC474426
0.8992	High Similarity	NPC474425
0.8984	High Similarity	NPC17681
0.896	High Similarity	NPC471559
0.8926	High Similarity	NPC131801
0.8915	High Similarity	NPC45358
0.888	High Similarity	NPC243269
0.8819	High Similarity	NPC473355
0.8819	High Similarity	NPC471554
0.8819	High Similarity	NPC471573
0.8819	High Similarity	NPC471501
0.873	High Similarity	NPC118853
0.872	High Similarity	NPC473379
0.872	High Similarity	NPC471549
0.8712	High Similarity	NPC14650
0.8672	High Similarity	NPC137570
0.8667	High Similarity	NPC26157
0.8667	High Similarity	NPC1811
0.8647	High Similarity	NPC303217
0.8636	High Similarity	NPC288209
0.8583	High Similarity	NPC188377
0.8583	High Similarity	NPC65735
0.8583	High Similarity	NPC105249
0.8462	Intermediate Similarity	NPC112706
0.8462	Intermediate Similarity	NPC207294
0.8456	Intermediate Similarity	NPC107571
0.845	Intermediate Similarity	NPC138139
0.845	Intermediate Similarity	NPC46536
0.8444	Intermediate Similarity	NPC473268
0.8409	Intermediate Similarity	NPC89133
0.84	Intermediate Similarity	NPC21831
0.84	Intermediate Similarity	NPC187547
0.8385	Intermediate Similarity	NPC83178
0.8346	Intermediate Similarity	NPC471544
0.8346	Intermediate Similarity	NPC473344
0.8346	Intermediate Similarity	NPC471545
0.8333	Intermediate Similarity	NPC471521
0.8333	Intermediate Similarity	NPC473356
0.8306	Intermediate Similarity	NPC28054
0.8296	Intermediate Similarity	NPC159786
0.8286	Intermediate Similarity	NPC307346
0.8286	Intermediate Similarity	NPC218712
0.8286	Intermediate Similarity	NPC261733
0.8286	Intermediate Similarity	NPC267004
0.8281	Intermediate Similarity	NPC477967
0.8264	Intermediate Similarity	NPC177331
0.8231	Intermediate Similarity	NPC179354
0.8217	Intermediate Similarity	NPC16922
0.8203	Intermediate Similarity	NPC1848
0.8189	Intermediate Similarity	NPC4898
0.8188	Intermediate Similarity	NPC90953
0.8168	Intermediate Similarity	NPC23086
0.8162	Intermediate Similarity	NPC476947
0.814	Intermediate Similarity	NPC263870
0.8088	Intermediate Similarity	NPC106247
0.8085	Intermediate Similarity	NPC80635
0.8085	Intermediate Similarity	NPC254198
0.8074	Intermediate Similarity	NPC473982
0.8062	Intermediate Similarity	NPC79557
0.8043	Intermediate Similarity	NPC186626
0.8042	Intermediate Similarity	NPC104924
0.8031	Intermediate Similarity	NPC312525
0.8031	Intermediate Similarity	NPC217180
0.803	Intermediate Similarity	NPC74612
0.8016	Intermediate Similarity	NPC150895
0.8015	Intermediate Similarity	NPC477965
0.8015	Intermediate Similarity	NPC470740
0.8015	Intermediate Similarity	NPC218838
0.8015	Intermediate Similarity	NPC477038
0.8014	Intermediate Similarity	NPC121158
0.8	Intermediate Similarity	NPC136340
0.8	Intermediate Similarity	NPC69647
0.8	Intermediate Similarity	NPC234494
0.8	Intermediate Similarity	NPC125182
0.8	Intermediate Similarity	NPC298190
0.8	Intermediate Similarity	NPC317217
0.7986	Intermediate Similarity	NPC255414
0.797	Intermediate Similarity	NPC95567
0.797	Intermediate Similarity	NPC319140
0.7969	Intermediate Similarity	NPC243704
0.7969	Intermediate Similarity	NPC291619
0.7969	Intermediate Similarity	NPC254958
0.7959	Intermediate Similarity	NPC474219
0.7959	Intermediate Similarity	NPC33938
0.7959	Intermediate Similarity	NPC474378
0.7958	Intermediate Similarity	NPC476946
0.7953	Intermediate Similarity	NPC45536
0.7945	Intermediate Similarity	NPC228842
0.7941	Intermediate Similarity	NPC471817
0.7929	Intermediate Similarity	NPC202260
0.7917	Intermediate Similarity	NPC346
0.791	Intermediate Similarity	NPC477966
0.791	Intermediate Similarity	NPC477039
0.791	Intermediate Similarity	NPC477040
0.791	Intermediate Similarity	NPC477123
0.7902	Intermediate Similarity	NPC137295
0.7902	Intermediate Similarity	NPC251865
0.7899	Intermediate Similarity	NPC92941
0.7891	Intermediate Similarity	NPC227660
0.7879	Intermediate Similarity	NPC130275
0.7874	Intermediate Similarity	NPC205523
0.7868	Intermediate Similarity	NPC475092
0.7868	Intermediate Similarity	NPC61788
0.7852	Intermediate Similarity	NPC223063
0.7852	Intermediate Similarity	NPC120836
0.7847	Intermediate Similarity	NPC195920
0.7847	Intermediate Similarity	NPC34056
0.7842	Intermediate Similarity	NPC146872
0.7838	Intermediate Similarity	NPC121615
0.7838	Intermediate Similarity	NPC294511
0.7838	Intermediate Similarity	NPC268905
0.7838	Intermediate Similarity	NPC44577
0.7836	Intermediate Similarity	NPC290955
0.7832	Intermediate Similarity	NPC267632
0.7823	Intermediate Similarity	NPC470997
0.7815	Intermediate Similarity	NPC472779
0.7812	Intermediate Similarity	NPC476031
0.7812	Intermediate Similarity	NPC476014
0.7808	Intermediate Similarity	NPC7388
0.78	Intermediate Similarity	NPC469485
0.7794	Intermediate Similarity	NPC21460
0.7794	Intermediate Similarity	NPC476925
0.7786	Intermediate Similarity	NPC470742
0.7786	Intermediate Similarity	NPC307401
0.7786	Intermediate Similarity	NPC278832
0.7786	Intermediate Similarity	NPC64157
0.7785	Intermediate Similarity	NPC34421
0.7785	Intermediate Similarity	NPC237259
0.7785	Intermediate Similarity	NPC302054
0.7785	Intermediate Similarity	NPC253201
0.7785	Intermediate Similarity	NPC98206
0.7778	Intermediate Similarity	NPC476917
0.7778	Intermediate Similarity	NPC327527
0.7778	Intermediate Similarity	NPC26532
0.7778	Intermediate Similarity	NPC329707
0.7778	Intermediate Similarity	NPC476944
0.7778	Intermediate Similarity	NPC279877
0.777	Intermediate Similarity	NPC158525
0.7762	Intermediate Similarity	NPC52412
0.7755	Intermediate Similarity	NPC470998
0.7748	Intermediate Similarity	NPC194499
0.7748	Intermediate Similarity	NPC472777
0.7748	Intermediate Similarity	NPC472778
0.7748	Intermediate Similarity	NPC472776
0.7748	Intermediate Similarity	NPC7059
0.7748	Intermediate Similarity	NPC173544
0.7748	Intermediate Similarity	NPC88007
0.7748	Intermediate Similarity	NPC470118
0.7748	Intermediate Similarity	NPC261597
0.7746	Intermediate Similarity	NPC67003
0.7746	Intermediate Similarity	NPC90296
0.7746	Intermediate Similarity	NPC56197
0.7746	Intermediate Similarity	NPC282973
0.7746	Intermediate Similarity	NPC148374
0.774	Intermediate Similarity	NPC216755
0.774	Intermediate Similarity	NPC250228
0.774	Intermediate Similarity	NPC471174
0.7737	Intermediate Similarity	NPC477645
0.7733	Intermediate Similarity	NPC296807
0.7733	Intermediate Similarity	NPC44675
0.7733	Intermediate Similarity	NPC155939
0.7733	Intermediate Similarity	NPC214541
0.7733	Intermediate Similarity	NPC141538
0.773	Intermediate Similarity	NPC236532
0.7727	Intermediate Similarity	NPC36255
0.7724	Intermediate Similarity	NPC5676
0.7724	Intermediate Similarity	NPC469642
0.7721	Intermediate Similarity	NPC208389
0.7718	Intermediate Similarity	NPC472672
0.7714	Intermediate Similarity	NPC204592
0.7714	Intermediate Similarity	NPC46896
0.7708	Intermediate Similarity	NPC22248
0.7708	Intermediate Similarity	NPC110305
0.7704	Intermediate Similarity	NPC474476
0.7704	Intermediate Similarity	NPC246392
0.7703	Intermediate Similarity	NPC212257
0.7692	Intermediate Similarity	NPC293424

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 NPC474279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	936
0.2-0.3	1960
0.3-0.4	2627
0.4-0.5	2053
0.5-0.6	1028
0.6-0.7	321
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
0.7676	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.7447	Intermediate Similarity	NPD6355	Discontinued
0.7279	Intermediate Similarity	NPD9717	Approved
0.7273	Intermediate Similarity	NPD5761	Phase 2
0.7273	Intermediate Similarity	NPD5760	Phase 2
0.7214	Intermediate Similarity	NPD6832	Phase 2
0.7194	Intermediate Similarity	NPD5647	Approved
0.7172	Intermediate Similarity	NPD4308	Phase 3
0.7172	Intermediate Similarity	NPD2799	Discontinued
0.7153	Intermediate Similarity	NPD6653	Approved
0.7122	Intermediate Similarity	NPD2797	Approved
0.7121	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6798	Discontinued
0.7095	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD447	Suspended
0.7024	Intermediate Similarity	NPD8434	Phase 2
0.7021	Intermediate Similarity	NPD9494	Approved
0.702	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD2354	Approved
0.6993	Remote Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD2313	Discontinued
0.6963	Remote Similarity	NPD9092	Discovery
0.6959	Remote Similarity	NPD6002	Phase 3
0.6959	Remote Similarity	NPD6004	Phase 3
0.6959	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6005	Phase 3
0.6959	Remote Similarity	NPD2344	Approved
0.6944	Remote Similarity	NPD4062	Phase 3
0.6944	Remote Similarity	NPD6233	Phase 2
0.6943	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6273	Approved
0.6928	Remote Similarity	NPD6765	Approved
0.6928	Remote Similarity	NPD6764	Approved
0.6923	Remote Similarity	NPD7095	Approved
0.6918	Remote Similarity	NPD7075	Discontinued
0.6917	Remote Similarity	NPD1241	Discontinued
0.6912	Remote Similarity	NPD9545	Approved
0.6908	Remote Similarity	NPD6799	Approved
0.6906	Remote Similarity	NPD1608	Approved
0.6903	Remote Similarity	NPD7458	Discontinued
0.6897	Remote Similarity	NPD4307	Phase 2
0.6892	Remote Similarity	NPD2935	Discontinued
0.6887	Remote Similarity	NPD3887	Approved
0.6884	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD411	Approved
0.6875	Remote Similarity	NPD3764	Approved
0.6846	Remote Similarity	NPD1358	Approved
0.6842	Remote Similarity	NPD7440	Discontinued
0.6842	Remote Similarity	NPD7843	Approved
0.6831	Remote Similarity	NPD2798	Approved
0.6831	Remote Similarity	NPD1019	Discontinued
0.6826	Remote Similarity	NPD6559	Discontinued
0.6821	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4110	Phase 3
0.6821	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5049	Phase 3
0.6818	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7157	Approved
0.6806	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5958	Discontinued
0.6795	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2684	Approved
0.6788	Remote Similarity	NPD1894	Discontinued
0.6781	Remote Similarity	NPD4060	Phase 1
0.6776	Remote Similarity	NPD2309	Approved
0.6774	Remote Similarity	NPD920	Approved
0.6774	Remote Similarity	NPD5403	Approved
0.6769	Remote Similarity	NPD3134	Approved
0.6765	Remote Similarity	NPD6785	Approved
0.6765	Remote Similarity	NPD6784	Approved
0.6765	Remote Similarity	NPD9493	Approved
0.6761	Remote Similarity	NPD6362	Approved
0.6759	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7097	Phase 1
0.6752	Remote Similarity	NPD6599	Discontinued
0.6735	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1933	Approved
0.6733	Remote Similarity	NPD2353	Approved
0.6733	Remote Similarity	NPD2346	Discontinued
0.6733	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD643	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7003	Approved
0.6711	Remote Similarity	NPD7033	Discontinued
0.6711	Remote Similarity	NPD3750	Approved
0.6691	Remote Similarity	NPD17	Approved
0.6691	Remote Similarity	NPD1778	Approved
0.669	Remote Similarity	NPD1876	Approved
0.6689	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD919	Approved
0.6646	Remote Similarity	NPD3882	Suspended
0.6646	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7768	Phase 2
0.6645	Remote Similarity	NPD5401	Approved
0.6645	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD987	Approved
0.6643	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6625	Remote Similarity	NPD7819	Suspended
0.6623	Remote Similarity	NPD5762	Approved
0.6623	Remote Similarity	NPD5763	Approved
0.6621	Remote Similarity	NPD2614	Approved
0.6619	Remote Similarity	NPD5585	Approved
0.6617	Remote Similarity	NPD2067	Discontinued
0.6605	Remote Similarity	NPD3749	Approved
0.6604	Remote Similarity	NPD7411	Suspended
0.6601	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1535	Discovery
0.6584	Remote Similarity	NPD5402	Approved
0.6579	Remote Similarity	NPD2424	Discontinued
0.6573	Remote Similarity	NPD1283	Approved
0.6566	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2239	Approved
0.6556	Remote Similarity	NPD4477	Approved
0.6556	Remote Similarity	NPD2240	Approved
0.6556	Remote Similarity	NPD4476	Approved
0.6549	Remote Similarity	NPD3972	Approved
0.6541	Remote Similarity	NPD2182	Approved
0.6538	Remote Similarity	NPD4661	Approved
0.6538	Remote Similarity	NPD4662	Approved
0.6538	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1243	Approved
0.6525	Remote Similarity	NPD3847	Discontinued
0.6513	Remote Similarity	NPD1471	Phase 3
0.651	Remote Similarity	NPD230	Phase 1
0.6503	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6677	Suspended
0.6496	Remote Similarity	NPD2629	Approved
0.6494	Remote Similarity	NPD8166	Discontinued
0.649	Remote Similarity	NPD3748	Approved
0.6486	Remote Similarity	NPD8032	Phase 2
0.6485	Remote Similarity	NPD8127	Discontinued
0.6481	Remote Similarity	NPD3817	Phase 2
0.6481	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3226	Approved
0.6471	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5535	Approved
0.6471	Remote Similarity	NPD1549	Phase 2
0.6466	Remote Similarity	NPD290	Approved
0.6463	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1934	Approved
0.646	Remote Similarity	NPD7577	Discontinued
0.6458	Remote Similarity	NPD3225	Approved
0.6456	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD4626	Approved
0.6449	Remote Similarity	NPD6671	Approved
0.6447	Remote Similarity	NPD2796	Approved
0.6447	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6032	Approved
0.6447	Remote Similarity	NPD2438	Suspended
0.6443	Remote Similarity	NPD3140	Approved
0.6443	Remote Similarity	NPD3142	Approved
0.6443	Remote Similarity	NPD2979	Phase 3
0.6438	Remote Similarity	NPD4380	Phase 2
0.6438	Remote Similarity	NPD454	Approved
0.6433	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2533	Approved
0.6433	Remote Similarity	NPD2532	Approved
0.6433	Remote Similarity	NPD2534	Approved
0.642	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4340	Discontinued
0.64	Remote Similarity	NPD4618	Approved
0.64	Remote Similarity	NPD4622	Approved
0.6398	Remote Similarity	NPD958	Approved
0.6391	Remote Similarity	NPD3818	Discontinued
0.6389	Remote Similarity	NPD4359	Approved
0.6386	Remote Similarity	NPD7199	Phase 2
0.6383	Remote Similarity	NPD5691	Approved
0.6382	Remote Similarity	NPD1510	Phase 2
0.638	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2649	Approved
0.6375	Remote Similarity	NPD3455	Phase 2
0.6375	Remote Similarity	NPD2651	Approved
0.6364	Remote Similarity	NPD1281	Approved
0.6364	Remote Similarity	NPD2897	Discontinued
0.6364	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD8313	Approved
0.6358	Remote Similarity	NPD8312	Approved
0.6353	Remote Similarity	NPD5844	Phase 1
0.6352	Remote Similarity	NPD3873	Phase 3
0.6352	Remote Similarity	NPD3869	Phase 3
0.6347	Remote Similarity	NPD6808	Phase 2
0.634	Remote Similarity	NPD5712	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