NPASS Compound

Structure

CID317869 OpenBabel06191716142D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.0293 4.8118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 4.7923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6842 -0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4829 3.3919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6840 1.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5015 0.5016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4974 1.4590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8423 3.3645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8207 3.3786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8536 4.3229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6740 0.0182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6525 2.9051 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8448 1.4460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0068 2.8951 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6596 1.9427 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8325 0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0124 1.9324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8321 1.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8270 0.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6554 -0.0121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0028 -0.9618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 8 10 2 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 11 3 1 6 0 0 0 11 16 1 0 0 0 0 12 4 1 6 0 0 0 12 15 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 8 1 6 0 0 0 14 17 1 0 0 0 0 15 7 1 1 0 0 0 15 18 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	335.841
LogP:	6.169
LogD:	3.841
LogS:	-3.637
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	4.277
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	1.5312301911762916e-05
Pgp-inhibitor:	0.865
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.371
Plasma Protein Binding (PPB):	98.36650848388672%
Volume Distribution (VD):	6.502
Pgp-substrate:	4.59040641784668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.401
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.312
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.675
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.606

ADMET: Excretion

Clearance (CL):	12.744
Half-life (T1/2):	0.221

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.856
Drug-inuced Liver Injury (DILI):	0.507
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.899
Carcinogencity:	0.547
Eye Corrosion:	0.014
Eye Irritation:	0.847
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC317869

Natural Product ID:	NPC317869
*Common Name:**	(4S,6S,6Ar,9S)-3,6,9-Trimethyl-4-(2-Methylprop-1-Enyl)-5,6,6A,7,8,9-Hexahydro-4H-Phenalene-1,2-Diol
IUPAC Name:	(4S,6S,6aR,9S)-3,6,9-trimethyl-4-(2-methylprop-1-enyl)-5,6,6a,7,8,9-hexahydro-4H-phenalene-1,2-diol
Synonyms:
Standard InCHIKey:	QYYIMVMYWAMAAS-DDHJSBNISA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-10(2)8-14-9-12(4)15-7-6-11(3)16-18(15)17(14)13(5)19(21)20(16)22/h8,11-12,14-15,21-22H,6-7,9H2,1-5H3/t11-,12-,14+,15+/m0/s1
SMILES:	CC(=C[C@@H]1C[C@H](C)[C@@H]2c3c1c(C)c(O)c(c3[C@H](CC2)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1355602
PubChem CID:	11483440
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003398] Amphilectane, neoamphilectane, cycloamphilectane, and adociane 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
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[10425124]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10822593]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[11170678]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828474]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	Colombian	n.a.	PMID[15497938]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715964]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21978379]

☑ 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
Potency	21

Activity Type	# Activity
Cell Line	1
Individual Protein	14
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[543793]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[543793]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[543793]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[543793]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[543793]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[543793]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[543793]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[543793]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[543793]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[543793]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[543793]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	10000.0	nM	PMID[543793]
NPT2	Others	Unspecified		Potency	=	92.0	nM	PMID[543793]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[543793]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[543793]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	89125.1	nM	PMID[543793]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[543793]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3696.4	nM	PMID[543793]
NPT2	Others	Unspecified		Potency	n.a.	1258.9	nM	PMID[543793]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[543793]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	26679.5	nM	PMID[543793]

☑ 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 NPC317869 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	321
0.1-0.2	1751
0.2-0.3	4443
0.3-0.4	12955
0.4-0.5	7628
0.5-0.6	9174
0.6-0.7	5136
0.7-0.8	1169
0.8-0.85	99
0.85-0.9	18
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC471179
0.9279	High Similarity	NPC16030
0.8947	High Similarity	NPC176893
0.8909	High Similarity	NPC260323
0.8909	High Similarity	NPC176279
0.8889	High Similarity	NPC151477
0.8879	High Similarity	NPC474115
0.8829	High Similarity	NPC46940
0.8814	High Similarity	NPC224342
0.8803	High Similarity	NPC471794
0.8761	High Similarity	NPC192948
0.8761	High Similarity	NPC35797
0.875	High Similarity	NPC715
0.8739	High Similarity	NPC95716
0.8704	High Similarity	NPC117115
0.8684	High Similarity	NPC308311
0.8684	High Similarity	NPC38893
0.8684	High Similarity	NPC471668
0.8684	High Similarity	NPC477137
0.8678	High Similarity	NPC201069
0.8673	High Similarity	NPC195922
0.8661	High Similarity	NPC250323
0.8649	High Similarity	NPC141782
0.8636	High Similarity	NPC11554
0.8624	High Similarity	NPC21594
0.8609	High Similarity	NPC304510
0.8609	High Similarity	NPC172219
0.8571	High Similarity	NPC151537
0.8559	High Similarity	NPC228343
0.8559	High Similarity	NPC254833
0.8559	High Similarity	NPC58865
0.8534	High Similarity	NPC471671
0.8522	High Similarity	NPC92
0.8522	High Similarity	NPC219112
0.8522	High Similarity	NPC469663
0.8509	High Similarity	NPC268160
0.8487	Intermediate Similarity	NPC321402
0.8482	Intermediate Similarity	NPC13482
0.8482	Intermediate Similarity	NPC132720
0.8468	Intermediate Similarity	NPC291001
0.8468	Intermediate Similarity	NPC312341
0.8468	Intermediate Similarity	NPC233835
0.8462	Intermediate Similarity	NPC469644
0.8462	Intermediate Similarity	NPC93071
0.8462	Intermediate Similarity	NPC126002
0.8462	Intermediate Similarity	NPC191866
0.8448	Intermediate Similarity	NPC477136
0.8443	Intermediate Similarity	NPC476536
0.8435	Intermediate Similarity	NPC147179
0.8435	Intermediate Similarity	NPC469719
0.8403	Intermediate Similarity	NPC237667
0.8403	Intermediate Similarity	NPC39029
0.8393	Intermediate Similarity	NPC314187
0.8387	Intermediate Similarity	NPC99795
0.8364	Intermediate Similarity	NPC239291
0.8362	Intermediate Similarity	NPC308828
0.8347	Intermediate Similarity	NPC15127
0.8333	Intermediate Similarity	NPC111845
0.8333	Intermediate Similarity	NPC227719
0.832	Intermediate Similarity	NPC78575
0.8319	Intermediate Similarity	NPC24125
0.8293	Intermediate Similarity	NPC471077
0.8291	Intermediate Similarity	NPC277588
0.8291	Intermediate Similarity	NPC299180
0.8288	Intermediate Similarity	NPC271274
0.8288	Intermediate Similarity	NPC477814
0.8279	Intermediate Similarity	NPC228771
0.8279	Intermediate Similarity	NPC29008
0.8279	Intermediate Similarity	NPC266705
0.8273	Intermediate Similarity	NPC238696
0.8268	Intermediate Similarity	NPC293454
0.8264	Intermediate Similarity	NPC53567
0.8261	Intermediate Similarity	NPC322239
0.8254	Intermediate Similarity	NPC59239
0.8254	Intermediate Similarity	NPC228843
0.825	Intermediate Similarity	NPC162935
0.825	Intermediate Similarity	NPC249340
0.8246	Intermediate Similarity	NPC77772
0.8246	Intermediate Similarity	NPC322753
0.8235	Intermediate Similarity	NPC475245
0.822	Intermediate Similarity	NPC154030
0.822	Intermediate Similarity	NPC469609
0.822	Intermediate Similarity	NPC144343
0.8203	Intermediate Similarity	NPC153088
0.8189	Intermediate Similarity	NPC138472
0.8182	Intermediate Similarity	NPC196479
0.8182	Intermediate Similarity	NPC11250
0.8175	Intermediate Similarity	NPC243305
0.8167	Intermediate Similarity	NPC259703
0.8167	Intermediate Similarity	NPC32322
0.8158	Intermediate Similarity	NPC296683
0.8151	Intermediate Similarity	NPC217174
0.8151	Intermediate Similarity	NPC151197
0.814	Intermediate Similarity	NPC68292
0.813	Intermediate Similarity	NPC9067
0.812	Intermediate Similarity	NPC84999
0.812	Intermediate Similarity	NPC246760
0.8115	Intermediate Similarity	NPC471187
0.8108	Intermediate Similarity	NPC272029
0.8108	Intermediate Similarity	NPC471511
0.8108	Intermediate Similarity	NPC120719
0.8103	Intermediate Similarity	NPC263753
0.8099	Intermediate Similarity	NPC154696
0.8091	Intermediate Similarity	NPC51015
0.8087	Intermediate Similarity	NPC470770
0.8087	Intermediate Similarity	NPC469912
0.8087	Intermediate Similarity	NPC266937
0.8083	Intermediate Similarity	NPC260832
0.8083	Intermediate Similarity	NPC135467
0.8083	Intermediate Similarity	NPC478121
0.808	Intermediate Similarity	NPC307050
0.808	Intermediate Similarity	NPC277458
0.807	Intermediate Similarity	NPC55617
0.807	Intermediate Similarity	NPC62258
0.8067	Intermediate Similarity	NPC206
0.8051	Intermediate Similarity	NPC141001
0.8049	Intermediate Similarity	NPC181334
0.8047	Intermediate Similarity	NPC476282
0.8036	Intermediate Similarity	NPC138942
0.8034	Intermediate Similarity	NPC471534
0.8034	Intermediate Similarity	NPC120280
0.8034	Intermediate Similarity	NPC107240
0.8034	Intermediate Similarity	NPC249270
0.8033	Intermediate Similarity	NPC176208
0.8033	Intermediate Similarity	NPC71094
0.8033	Intermediate Similarity	NPC30462
0.8018	Intermediate Similarity	NPC168829
0.8017	Intermediate Similarity	NPC241001
0.8017	Intermediate Similarity	NPC228425
0.8017	Intermediate Similarity	NPC62867
0.8017	Intermediate Similarity	NPC177962
0.8	Intermediate Similarity	NPC224870
0.8	Intermediate Similarity	NPC147634
0.8	Intermediate Similarity	NPC120982
0.8	Intermediate Similarity	NPC79793
0.8	Intermediate Similarity	NPC211885
0.8	Intermediate Similarity	NPC174096
0.8	Intermediate Similarity	NPC72729
0.8	Intermediate Similarity	NPC226401
0.7984	Intermediate Similarity	NPC137750
0.7983	Intermediate Similarity	NPC278652
0.7982	Intermediate Similarity	NPC6597
0.7982	Intermediate Similarity	NPC77492
0.7982	Intermediate Similarity	NPC109955
0.7982	Intermediate Similarity	NPC79241
0.7966	Intermediate Similarity	NPC472893
0.7966	Intermediate Similarity	NPC474486
0.7951	Intermediate Similarity	NPC253627
0.7951	Intermediate Similarity	NPC475166
0.7951	Intermediate Similarity	NPC77569
0.7951	Intermediate Similarity	NPC142198
0.7949	Intermediate Similarity	NPC471485
0.7949	Intermediate Similarity	NPC321589
0.7949	Intermediate Similarity	NPC117846
0.7946	Intermediate Similarity	NPC288411
0.7939	Intermediate Similarity	NPC242715
0.7939	Intermediate Similarity	NPC56329
0.7939	Intermediate Similarity	NPC22902
0.7937	Intermediate Similarity	NPC23012
0.7934	Intermediate Similarity	NPC103916
0.7931	Intermediate Similarity	NPC187583
0.7931	Intermediate Similarity	NPC179002
0.7931	Intermediate Similarity	NPC257430
0.7923	Intermediate Similarity	NPC103082
0.7923	Intermediate Similarity	NPC313081
0.792	Intermediate Similarity	NPC43000
0.792	Intermediate Similarity	NPC325294
0.792	Intermediate Similarity	NPC321822
0.792	Intermediate Similarity	NPC470724
0.792	Intermediate Similarity	NPC100414
0.7917	Intermediate Similarity	NPC164649
0.7917	Intermediate Similarity	NPC48342
0.7903	Intermediate Similarity	NPC199273
0.7899	Intermediate Similarity	NPC261973
0.7895	Intermediate Similarity	NPC320439
0.7895	Intermediate Similarity	NPC471853
0.789	Intermediate Similarity	NPC259512
0.789	Intermediate Similarity	NPC312132
0.7886	Intermediate Similarity	NPC121168
0.7886	Intermediate Similarity	NPC297057
0.7879	Intermediate Similarity	NPC275061
0.7879	Intermediate Similarity	NPC243996
0.7879	Intermediate Similarity	NPC132804
0.7879	Intermediate Similarity	NPC230811
0.7879	Intermediate Similarity	NPC220344
0.7876	Intermediate Similarity	NPC99557
0.7876	Intermediate Similarity	NPC219286
0.7869	Intermediate Similarity	NPC129176
0.7869	Intermediate Similarity	NPC328504
0.7863	Intermediate Similarity	NPC30632
0.7863	Intermediate Similarity	NPC302371
0.7857	Intermediate Similarity	NPC78364
0.7857	Intermediate Similarity	NPC69424
0.7857	Intermediate Similarity	NPC108164
0.7857	Intermediate Similarity	NPC176130
0.7857	Intermediate Similarity	NPC84672
0.7851	Intermediate Similarity	NPC281298
0.7851	Intermediate Similarity	NPC42657
0.7851	Intermediate Similarity	NPC310338
0.7846	Intermediate Similarity	NPC209199

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 NPC317869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	1046
0.2-0.3	1709
0.3-0.4	3098
0.4-0.5	1666
0.5-0.6	962
0.6-0.7	287
0.7-0.8	51
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD3022	Approved
0.8559	High Similarity	NPD3021	Approved
0.8378	Intermediate Similarity	NPD2342	Discontinued
0.8333	Intermediate Similarity	NPD7635	Approved
0.7951	Intermediate Similarity	NPD3092	Approved
0.7917	Intermediate Similarity	NPD3091	Approved
0.7909	Intermediate Similarity	NPD3020	Approved
0.789	Intermediate Similarity	NPD288	Approved
0.7829	Intermediate Similarity	NPD3620	Phase 2
0.7829	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1809	Phase 2
0.7798	Intermediate Similarity	NPD844	Approved
0.7787	Intermediate Similarity	NPD3019	Approved
0.7787	Intermediate Similarity	NPD4059	Approved
0.7778	Intermediate Similarity	NPD845	Approved
0.7759	Intermediate Similarity	NPD4750	Phase 3
0.7698	Intermediate Similarity	NPD3094	Phase 2
0.7642	Intermediate Similarity	NPD2286	Discontinued
0.7642	Intermediate Similarity	NPD2932	Approved
0.7636	Intermediate Similarity	NPD2860	Approved
0.7636	Intermediate Similarity	NPD2859	Approved
0.7609	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4093	Discontinued
0.7545	Intermediate Similarity	NPD2934	Approved
0.7545	Intermediate Similarity	NPD2933	Approved
0.754	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3095	Discontinued
0.75	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7340	Approved
0.7459	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2420	Approved
0.741	Intermediate Similarity	NPD2421	Approved
0.7387	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4626	Approved
0.7355	Intermediate Similarity	NPD1398	Phase 1
0.7333	Intermediate Similarity	NPD228	Approved
0.7313	Intermediate Similarity	NPD4097	Suspended
0.7308	Intermediate Similarity	NPD5736	Approved
0.7293	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1751	Approved
0.7213	Intermediate Similarity	NPD5283	Phase 1
0.7197	Intermediate Similarity	NPD4625	Phase 3
0.7194	Intermediate Similarity	NPD8166	Discontinued
0.719	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1792	Phase 2
0.7165	Intermediate Similarity	NPD3023	Approved
0.7165	Intermediate Similarity	NPD3026	Approved
0.7155	Intermediate Similarity	NPD940	Approved
0.7155	Intermediate Similarity	NPD846	Approved
0.7154	Intermediate Similarity	NPD497	Approved
0.7143	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD3025	Approved
0.7131	Intermediate Similarity	NPD9377	Approved
0.7131	Intermediate Similarity	NPD9379	Approved
0.7121	Intermediate Similarity	NPD2606	Approved
0.7121	Intermediate Similarity	NPD2605	Approved
0.7113	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3645	Discontinued
0.7109	Intermediate Similarity	NPD1201	Approved
0.7101	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4624	Approved
0.7094	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6663	Approved
0.7073	Intermediate Similarity	NPD2229	Approved
0.7073	Intermediate Similarity	NPD2228	Approved
0.7073	Intermediate Similarity	NPD2234	Approved
0.7073	Intermediate Similarity	NPD498	Approved
0.7073	Intermediate Similarity	NPD495	Approved
0.7073	Intermediate Similarity	NPD496	Approved
0.7073	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5155	Approved
0.7068	Intermediate Similarity	NPD5156	Approved
0.7063	Intermediate Similarity	NPD5304	Approved
0.7063	Intermediate Similarity	NPD5303	Approved
0.7045	Intermediate Similarity	NPD3637	Approved
0.7045	Intermediate Similarity	NPD3636	Approved
0.7045	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3635	Approved
0.7029	Intermediate Similarity	NPD5406	Approved
0.7029	Intermediate Similarity	NPD5405	Approved
0.7029	Intermediate Similarity	NPD5408	Approved
0.7029	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5404	Approved
0.7023	Intermediate Similarity	NPD3055	Approved
0.7023	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3053	Approved
0.7008	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD4749	Approved
0.6992	Remote Similarity	NPD3595	Approved
0.6992	Remote Similarity	NPD3594	Approved
0.6992	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5735	Approved
0.6972	Remote Similarity	NPD3845	Phase 1
0.6972	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2195	Approved
0.697	Remote Similarity	NPD2194	Approved
0.6957	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4589	Approved
0.6947	Remote Similarity	NPD6696	Suspended
0.6947	Remote Similarity	NPD5311	Approved
0.6947	Remote Similarity	NPD1283	Approved
0.6947	Remote Similarity	NPD5310	Approved
0.694	Remote Similarity	NPD3027	Phase 3
0.6929	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1242	Phase 1
0.6917	Remote Similarity	NPD1444	Approved
0.6917	Remote Similarity	NPD1445	Approved
0.6894	Remote Similarity	NPD1470	Approved
0.6889	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD111	Approved
0.6879	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1651	Approved
0.687	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5327	Phase 3
0.6861	Remote Similarity	NPD3657	Discovery
0.6842	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7742	Approved
0.6835	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7743	Approved
0.6829	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6671	Approved
0.6806	Remote Similarity	NPD7390	Discontinued
0.6797	Remote Similarity	NPD7330	Discontinued
0.6791	Remote Similarity	NPD2861	Phase 2
0.6788	Remote Similarity	NPD4140	Approved
0.6788	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1613	Approved
0.6765	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4908	Phase 1
0.6738	Remote Similarity	NPD4721	Approved
0.6738	Remote Similarity	NPD4725	Approved
0.6738	Remote Similarity	NPD4726	Approved
0.6719	Remote Similarity	NPD7644	Approved
0.6718	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1281	Approved
0.6713	Remote Similarity	NPD7003	Approved
0.6692	Remote Similarity	NPD9381	Approved
0.6692	Remote Similarity	NPD9384	Approved
0.6691	Remote Similarity	NPD6353	Approved
0.669	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7041	Phase 2
0.6667	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD2230	Approved
0.6667	Remote Similarity	NPD9500	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD2232	Approved
0.6667	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2233	Approved
0.6643	Remote Similarity	NPD3638	Discontinued
0.6641	Remote Similarity	NPD3143	Discontinued
0.6639	Remote Similarity	NPD3028	Approved
0.6621	Remote Similarity	NPD3300	Phase 2
0.6617	Remote Similarity	NPD1669	Approved
0.6617	Remote Similarity	NPD9622	Approved
0.6614	Remote Similarity	NPD5951	Approved
0.6593	Remote Similarity	NPD257	Approved
0.6593	Remote Similarity	NPD6584	Phase 3
0.6593	Remote Similarity	NPD258	Approved
0.6591	Remote Similarity	NPD1611	Approved
0.6591	Remote Similarity	NPD1610	Phase 2
0.6573	Remote Similarity	NPD4256	Phase 2
0.6573	Remote Similarity	NPD4257	Approved
0.6573	Remote Similarity	NPD7037	Approved
0.6571	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7095	Approved
0.6567	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD709	Approved
0.6556	Remote Similarity	NPD37	Approved
0.6552	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6100	Approved
0.6549	Remote Similarity	NPD6099	Approved
0.6547	Remote Similarity	NPD3062	Approved
0.6547	Remote Similarity	NPD3059	Approved
0.6547	Remote Similarity	NPD3061	Approved
0.6541	Remote Similarity	NPD3070	Discontinued
0.6538	Remote Similarity	NPD6232	Discontinued
0.6532	Remote Similarity	NPD2684	Approved
0.6522	Remote Similarity	NPD5111	Phase 2
0.6522	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5110	Phase 2
0.6522	Remote Similarity	NPD7985	Registered
0.6522	Remote Similarity	NPD5109	Approved
0.6519	Remote Similarity	NPD7473	Discontinued
0.6515	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7636	Approved
0.6512	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5762	Approved
0.6503	Remote Similarity	NPD7266	Discontinued
0.6503	Remote Similarity	NPD5763	Approved
0.6486	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6331	Phase 2

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