NPASS Compound

Structure

CID85595 OpenBabel06191715422D 31 35 0 0 1 0 0 0 0 0999 V2000 -3.3939 1.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3643 -3.9114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2300 -3.4114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5229 -0.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0245 -1.9559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2640 0.4823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6827 -2.9119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6819 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2039 -1.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8416 -2.4266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8408 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3634 -0.9694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6824 1.9395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6804 -0.9709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5220 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6807 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8419 1.4553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5235 -2.4262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6821 -0.9699 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9704 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2042 -2.4257 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8411 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5212 0.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3640 -2.9114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5232 -1.4552 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8413 -1.4557 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0291 1.9591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0704 -2.9253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3922 -0.0201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 31 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 24 2 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 6 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 21 27 1 6 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 30 1 6 0 0 0 23 28 1 0 0 0 0 24 31 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.31
Volume:	468.523
LogP:	6.7
LogD:	4.677
LogS:	-3.144
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	4.484
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.146
MDCK Permeability:	1.9909040929633193e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.365
Plasma Protein Binding (PPB):	95.05976104736328%
Volume Distribution (VD):	1.193
Pgp-substrate:	3.814357042312622%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.797
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.465
CYP2D6-inhibitor:	0.151
CYP2D6-substrate:	0.693
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.681

ADMET: Excretion

Clearance (CL):	20.866
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.529
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.809
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.909
Carcinogencity:	0.228
Eye Corrosion:	0.009
Eye Irritation:	0.365
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC85595

Natural Product ID:	NPC85595
*Common Name:**	Flabellinol
IUPAC Name:	(2S,4aS,4bS,6aS,11aS,11bS,13aR)-10-methoxy-1,1,4a,6a,9,11b-hexamethyl-3,4,4b,5,6,11,11a,12,13,13a-decahydro-2H-indeno[2,1-a]phenanthrene-2,7-diol
Synonyms:	Flabellinol
Standard InCHIKey:	PCJLFCANHKSKCL-XVDIEDCOSA-N
Standard InCHI:	InChI=1S/C28H42O3/c1-16-14-18(29)23-17(24(16)31-7)15-21-27(5)11-8-19-25(2,3)22(30)10-13-26(19,4)20(27)9-12-28(21,23)6/h14,19-22,29-30H,8-13,15H2,1-7H3/t19-,20+,21-,22-,26+,27-,28-/m0/s1
SMILES:	Cc1cc(c2c(C[C@H]3[C@@]4(C)CC[C@H]5C(C)(C)[C@H](CC[C@@]5(C)[C@H]4CC[C@]23C)O)c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513200
PubChem CID:	11304872
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s11306-014-0728-9]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/sdata.2014.29]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	Roots	Mexican	n.a.	PMID[10479311]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11171227]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12576668]
NPO20811	Stypopodium flabelliforme	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038542]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25245917]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	seed	n.a.	PMID[25891114]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	Database[MetaboLights]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18614	Gentiana turkestanorum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20473	Vaccinium membranaceum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16442	Omphalia campanella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21485	Polygala sibirica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18614	Gentiana turkestanorum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19772	Ceroplastes ceriferus	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20669	Baccharis rhetinodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21549	Consolida raveyi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14033	Torilis arvensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20811	Stypopodium flabelliforme	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4243	Didymocarpus leucocalyx	Species	Gesneriaceae	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
Others	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	LC50	=	9000.0	nM	PMID[479264]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	2000.0	nM	PMID[479264]
NPT2	Others	Unspecified		Activity	=	2.0	uM	PMID[479264]

☑ 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 NPC85595 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	425
0.1-0.2	1554
0.2-0.3	3326
0.3-0.4	8000
0.4-0.5	10489
0.5-0.6	9881
0.6-0.7	7790
0.7-0.8	1154
0.8-0.85	65
0.85-0.9	10
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9084	High Similarity	NPC27578
0.9084	High Similarity	NPC289624
0.8864	High Similarity	NPC153019
0.8788	High Similarity	NPC196193
0.875	High Similarity	NPC152946
0.8731	High Similarity	NPC211352
0.8702	High Similarity	NPC186889
0.8692	High Similarity	NPC4286
0.8692	High Similarity	NPC76119
0.8661	High Similarity	NPC260832
0.8661	High Similarity	NPC135467
0.8636	High Similarity	NPC47288
0.8623	High Similarity	NPC221134
0.8594	High Similarity	NPC129176
0.8571	High Similarity	NPC206028
0.8492	Intermediate Similarity	NPC469663
0.8492	Intermediate Similarity	NPC477137
0.8492	Intermediate Similarity	NPC38893
0.8492	Intermediate Similarity	NPC308311
0.8492	Intermediate Similarity	NPC92
0.8473	Intermediate Similarity	NPC248557
0.8456	Intermediate Similarity	NPC227719
0.8438	Intermediate Similarity	NPC469644
0.8421	Intermediate Similarity	NPC471077
0.8413	Intermediate Similarity	NPC35797
0.8413	Intermediate Similarity	NPC192948
0.8406	Intermediate Similarity	NPC68292
0.8385	Intermediate Similarity	NPC48623
0.8385	Intermediate Similarity	NPC168707
0.8382	Intermediate Similarity	NPC321502
0.837	Intermediate Similarity	NPC249425
0.8359	Intermediate Similarity	NPC471671
0.8358	Intermediate Similarity	NPC201069
0.8357	Intermediate Similarity	NPC473049
0.8357	Intermediate Similarity	NPC472794
0.8346	Intermediate Similarity	NPC33900
0.8346	Intermediate Similarity	NPC247858
0.8346	Intermediate Similarity	NPC137496
0.8346	Intermediate Similarity	NPC257540
0.8346	Intermediate Similarity	NPC154511
0.8346	Intermediate Similarity	NPC474387
0.8346	Intermediate Similarity	NPC219112
0.8346	Intermediate Similarity	NPC308828
0.8346	Intermediate Similarity	NPC470724
0.8346	Intermediate Similarity	NPC474358
0.832	Intermediate Similarity	NPC98372
0.8309	Intermediate Similarity	NPC258073
0.8308	Intermediate Similarity	NPC45663
0.8281	Intermediate Similarity	NPC477136
0.8281	Intermediate Similarity	NPC304510
0.8281	Intermediate Similarity	NPC172219
0.8271	Intermediate Similarity	NPC470726
0.8271	Intermediate Similarity	NPC124030
0.8268	Intermediate Similarity	NPC147179
0.8268	Intermediate Similarity	NPC469719
0.8244	Intermediate Similarity	NPC475839
0.8235	Intermediate Similarity	NPC470727
0.8231	Intermediate Similarity	NPC474131
0.8231	Intermediate Similarity	NPC103916
0.8231	Intermediate Similarity	NPC232295
0.8227	Intermediate Similarity	NPC76312
0.8222	Intermediate Similarity	NPC176590
0.8222	Intermediate Similarity	NPC223912
0.8217	Intermediate Similarity	NPC48342
0.8217	Intermediate Similarity	NPC469609
0.8217	Intermediate Similarity	NPC164649
0.8214	Intermediate Similarity	NPC98804
0.8203	Intermediate Similarity	NPC471668
0.8203	Intermediate Similarity	NPC312105
0.8195	Intermediate Similarity	NPC61685
0.8189	Intermediate Similarity	NPC268160
0.8182	Intermediate Similarity	NPC71094
0.8175	Intermediate Similarity	NPC312341
0.8169	Intermediate Similarity	NPC472791
0.8169	Intermediate Similarity	NPC472792
0.8168	Intermediate Similarity	NPC277798
0.8168	Intermediate Similarity	NPC100108
0.8168	Intermediate Similarity	NPC328504
0.816	Intermediate Similarity	NPC132720
0.8154	Intermediate Similarity	NPC93071
0.8154	Intermediate Similarity	NPC126002
0.8154	Intermediate Similarity	NPC32152
0.8143	Intermediate Similarity	NPC474610
0.8138	Intermediate Similarity	NPC471608
0.8129	Intermediate Similarity	NPC27394
0.8125	Intermediate Similarity	NPC283169
0.8112	Intermediate Similarity	NPC186033
0.8095	Intermediate Similarity	NPC77772
0.8095	Intermediate Similarity	NPC260323
0.8095	Intermediate Similarity	NPC275627
0.8095	Intermediate Similarity	NPC176279
0.8092	Intermediate Similarity	NPC68339
0.8077	Intermediate Similarity	NPC139047
0.8077	Intermediate Similarity	NPC154030
0.8062	Intermediate Similarity	NPC141001
0.8047	Intermediate Similarity	NPC470837
0.8045	Intermediate Similarity	NPC478058
0.8045	Intermediate Similarity	NPC46586
0.8045	Intermediate Similarity	NPC204535
0.8031	Intermediate Similarity	NPC177962
0.8031	Intermediate Similarity	NPC228425
0.8031	Intermediate Similarity	NPC62867
0.8027	Intermediate Similarity	NPC212142
0.8015	Intermediate Similarity	NPC323074
0.8015	Intermediate Similarity	NPC471449
0.8	Intermediate Similarity	NPC474599
0.8	Intermediate Similarity	NPC11266
0.8	Intermediate Similarity	NPC25648
0.8	Intermediate Similarity	NPC187993
0.8	Intermediate Similarity	NPC133407
0.8	Intermediate Similarity	NPC238176
0.8	Intermediate Similarity	NPC28476
0.7986	Intermediate Similarity	NPC321086
0.7986	Intermediate Similarity	NPC251549
0.7986	Intermediate Similarity	NPC59239
0.7986	Intermediate Similarity	NPC51262
0.7985	Intermediate Similarity	NPC474130
0.7985	Intermediate Similarity	NPC471187
0.7985	Intermediate Similarity	NPC261992
0.7973	Intermediate Similarity	NPC298647
0.7973	Intermediate Similarity	NPC273358
0.7972	Intermediate Similarity	NPC79372
0.7971	Intermediate Similarity	NPC99795
0.7971	Intermediate Similarity	NPC325003
0.7971	Intermediate Similarity	NPC472793
0.797	Intermediate Similarity	NPC77569
0.797	Intermediate Similarity	NPC142198
0.7956	Intermediate Similarity	NPC307050
0.7956	Intermediate Similarity	NPC277458
0.7955	Intermediate Similarity	NPC325544
0.7955	Intermediate Similarity	NPC477037
0.7955	Intermediate Similarity	NPC318581
0.7953	Intermediate Similarity	NPC266937
0.7953	Intermediate Similarity	NPC322753
0.7953	Intermediate Similarity	NPC470723
0.7953	Intermediate Similarity	NPC470770
0.7945	Intermediate Similarity	NPC90645
0.7945	Intermediate Similarity	NPC19862
0.7945	Intermediate Similarity	NPC235195
0.7945	Intermediate Similarity	NPC472457
0.7941	Intermediate Similarity	NPC325294
0.7941	Intermediate Similarity	NPC321822
0.7939	Intermediate Similarity	NPC63010
0.7933	Intermediate Similarity	NPC473018
0.7933	Intermediate Similarity	NPC120633
0.7926	Intermediate Similarity	NPC181334
0.7923	Intermediate Similarity	NPC236070
0.7923	Intermediate Similarity	NPC126759
0.7923	Intermediate Similarity	NPC69539
0.7923	Intermediate Similarity	NPC242580
0.7919	Intermediate Similarity	NPC195561
0.7919	Intermediate Similarity	NPC470619
0.7919	Intermediate Similarity	NPC470618
0.7919	Intermediate Similarity	NPC158784
0.7919	Intermediate Similarity	NPC208785
0.7919	Intermediate Similarity	NPC145527
0.7914	Intermediate Similarity	NPC237424
0.7914	Intermediate Similarity	NPC78575
0.7914	Intermediate Similarity	NPC238168
0.7914	Intermediate Similarity	NPC282508
0.791	Intermediate Similarity	NPC188997
0.791	Intermediate Similarity	NPC321402
0.791	Intermediate Similarity	NPC297057
0.7907	Intermediate Similarity	NPC471534
0.7907	Intermediate Similarity	NPC195922
0.7905	Intermediate Similarity	NPC96930
0.7905	Intermediate Similarity	NPC32017
0.7902	Intermediate Similarity	NPC265335
0.7899	Intermediate Similarity	NPC472797
0.7899	Intermediate Similarity	NPC266868
0.7895	Intermediate Similarity	NPC212559
0.7895	Intermediate Similarity	NPC96423
0.7891	Intermediate Similarity	NPC302371
0.7891	Intermediate Similarity	NPC215678
0.7891	Intermediate Similarity	NPC250323
0.7891	Intermediate Similarity	NPC274454
0.7887	Intermediate Similarity	NPC472649
0.7887	Intermediate Similarity	NPC191462
0.7887	Intermediate Similarity	NPC472647
0.7887	Intermediate Similarity	NPC472800
0.7887	Intermediate Similarity	NPC170328
0.7887	Intermediate Similarity	NPC472648
0.7887	Intermediate Similarity	NPC133463
0.7887	Intermediate Similarity	NPC206525
0.7883	Intermediate Similarity	NPC108164
0.7879	Intermediate Similarity	NPC151197
0.7879	Intermediate Similarity	NPC51341
0.7874	Intermediate Similarity	NPC141782
0.7872	Intermediate Similarity	NPC71372
0.7868	Intermediate Similarity	NPC105031
0.7868	Intermediate Similarity	NPC81641
0.7868	Intermediate Similarity	NPC252962
0.7868	Intermediate Similarity	NPC477213
0.7868	Intermediate Similarity	NPC293801
0.7867	Intermediate Similarity	NPC2745
0.7867	Intermediate Similarity	NPC302915
0.7857	Intermediate Similarity	NPC472798
0.7852	Intermediate Similarity	NPC292206
0.7847	Intermediate Similarity	NPC273623
0.7847	Intermediate Similarity	NPC164743

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 NPC85595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	899
0.2-0.3	1591
0.3-0.4	2779
0.4-0.5	1941
0.5-0.6	1106
0.6-0.7	429
0.7-0.8	58
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
0.8382	Intermediate Similarity	NPD3620	Phase 2
0.8382	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD5327	Phase 3
0.8217	Intermediate Similarity	NPD3091	Approved
0.8209	Intermediate Similarity	NPD4624	Approved
0.8195	Intermediate Similarity	NPD6696	Suspended
0.8188	Intermediate Similarity	NPD5735	Approved
0.8148	Intermediate Similarity	NPD2861	Phase 2
0.8129	Intermediate Similarity	NPD6353	Approved
0.8116	Intermediate Similarity	NPD4140	Approved
0.8	Intermediate Similarity	NPD4097	Suspended
0.797	Intermediate Similarity	NPD3092	Approved
0.7941	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD7340	Approved
0.7891	Intermediate Similarity	NPD7635	Approved
0.7868	Intermediate Similarity	NPD3094	Phase 2
0.7852	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD3095	Discontinued
0.7754	Intermediate Similarity	NPD5736	Approved
0.771	Intermediate Similarity	NPD6671	Approved
0.7692	Intermediate Similarity	NPD1398	Phase 1
0.7687	Intermediate Similarity	NPD4059	Approved
0.7687	Intermediate Similarity	NPD4626	Approved
0.7655	Intermediate Similarity	NPD5762	Approved
0.7655	Intermediate Similarity	NPD5763	Approved
0.76	Intermediate Similarity	NPD6273	Approved
0.7556	Intermediate Similarity	NPD3019	Approved
0.7552	Intermediate Similarity	NPD3657	Discovery
0.7551	Intermediate Similarity	NPD6674	Discontinued
0.7535	Intermediate Similarity	NPD6663	Approved
0.7518	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD7003	Approved
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7481	Intermediate Similarity	NPD5691	Approved
0.7467	Intermediate Similarity	NPD7041	Phase 2
0.7467	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD2932	Approved
0.7413	Intermediate Similarity	NPD8032	Phase 2
0.7407	Intermediate Similarity	NPD7741	Discontinued
0.7379	Intermediate Similarity	NPD2157	Approved
0.7368	Intermediate Similarity	NPD6090	Discontinued
0.7365	Intermediate Similarity	NPD7037	Approved
0.7364	Intermediate Similarity	NPD2342	Discontinued
0.7342	Intermediate Similarity	NPD7833	Phase 2
0.7342	Intermediate Similarity	NPD7831	Phase 2
0.7342	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4749	Approved
0.7324	Intermediate Similarity	NPD4908	Phase 1
0.732	Intermediate Similarity	NPD5699	Approved
0.7319	Intermediate Similarity	NPD1611	Approved
0.7312	Intermediate Similarity	NPD8127	Discontinued
0.7303	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1283	Approved
0.7279	Intermediate Similarity	NPD7742	Approved
0.7279	Intermediate Similarity	NPD7743	Approved
0.7266	Intermediate Similarity	NPD2233	Approved
0.7266	Intermediate Similarity	NPD2232	Approved
0.7266	Intermediate Similarity	NPD2230	Approved
0.7241	Intermediate Similarity	NPD2238	Phase 2
0.723	Intermediate Similarity	NPD6100	Approved
0.723	Intermediate Similarity	NPD6099	Approved
0.7226	Intermediate Similarity	NPD1651	Approved
0.7222	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7644	Approved
0.7185	Intermediate Similarity	NPD7157	Approved
0.7163	Intermediate Similarity	NPD8651	Approved
0.7154	Intermediate Similarity	NPD968	Approved
0.7152	Intermediate Similarity	NPD5929	Approved
0.7122	Intermediate Similarity	NPD3496	Discontinued
0.7115	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7458	Discontinued
0.7103	Intermediate Similarity	NPD7294	Phase 1
0.7103	Intermediate Similarity	NPD7985	Registered
0.7078	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1610	Phase 2
0.7071	Intermediate Similarity	NPD1281	Approved
0.7063	Intermediate Similarity	NPD288	Approved
0.7063	Intermediate Similarity	NPD6584	Phase 3
0.7037	Intermediate Similarity	NPD5283	Phase 1
0.7037	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3027	Phase 3
0.7021	Intermediate Similarity	NPD2235	Phase 2
0.7021	Intermediate Similarity	NPD2231	Phase 2
0.7007	Intermediate Similarity	NPD3109	Approved
0.7007	Intermediate Similarity	NPD3110	Approved
0.7007	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD3023	Approved
0.7	Intermediate Similarity	NPD3026	Approved
0.6993	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4750	Phase 3
0.6984	Remote Similarity	NPD1809	Phase 2
0.6984	Remote Similarity	NPD844	Approved
0.6981	Remote Similarity	NPD37	Approved
0.698	Remote Similarity	NPD7097	Phase 1
0.6978	Remote Similarity	NPD3025	Approved
0.6978	Remote Similarity	NPD3024	Approved
0.6978	Remote Similarity	NPD1357	Approved
0.6974	Remote Similarity	NPD3638	Discontinued
0.6972	Remote Similarity	NPD1669	Approved
0.6959	Remote Similarity	NPD6355	Discontinued
0.6953	Remote Similarity	NPD3020	Approved
0.695	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD709	Approved
0.6929	Remote Similarity	NPD1778	Approved
0.6928	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3892	Phase 2
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8166	Discontinued
0.6918	Remote Similarity	NPD7095	Approved
0.6917	Remote Similarity	NPD2684	Approved
0.6913	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6653	Approved
0.6912	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2237	Approved
0.6897	Remote Similarity	NPD1712	Approved
0.6892	Remote Similarity	NPD1613	Approved
0.6892	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6959	Discontinued
0.6889	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD228	Approved
0.6883	Remote Similarity	NPD8131	Suspended
0.6875	Remote Similarity	NPD5714	Approved
0.6871	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD27	Approved
0.6867	Remote Similarity	NPD2489	Approved
0.6866	Remote Similarity	NPD5451	Approved
0.6861	Remote Similarity	NPD497	Approved
0.6857	Remote Similarity	NPD5585	Approved
0.6855	Remote Similarity	NPD7028	Phase 2
0.6853	Remote Similarity	NPD6583	Phase 3
0.6853	Remote Similarity	NPD6582	Phase 2
0.6852	Remote Similarity	NPD4967	Phase 2
0.6852	Remote Similarity	NPD4966	Approved
0.6852	Remote Similarity	NPD4965	Approved
0.6849	Remote Similarity	NPD600	Approved
0.6849	Remote Similarity	NPD596	Approved
0.6848	Remote Similarity	NPD3051	Approved
0.6845	Remote Similarity	NPD5844	Phase 1
0.6842	Remote Similarity	NPD6002	Phase 3
0.6842	Remote Similarity	NPD290	Approved
0.6842	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6005	Phase 3
0.6842	Remote Similarity	NPD6004	Phase 3
0.6842	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7843	Approved
0.6825	Remote Similarity	NPD845	Approved
0.6821	Remote Similarity	NPD4108	Discontinued
0.6818	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4110	Phase 3
0.6818	Remote Similarity	NPD6331	Phase 2
0.6815	Remote Similarity	NPD2676	Approved
0.6815	Remote Similarity	NPD2675	Approved
0.6812	Remote Similarity	NPD6387	Discontinued
0.6809	Remote Similarity	NPD2286	Discontinued
0.6809	Remote Similarity	NPD2668	Approved
0.6809	Remote Similarity	NPD2667	Approved
0.6807	Remote Similarity	NPD2970	Approved
0.6807	Remote Similarity	NPD2969	Approved
0.6806	Remote Similarity	NPD1876	Approved
0.6794	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD496	Approved
0.6788	Remote Similarity	NPD495	Approved
0.6788	Remote Similarity	NPD498	Approved
0.6786	Remote Similarity	NPD7228	Approved
0.6786	Remote Similarity	NPD1548	Phase 1
0.6776	Remote Similarity	NPD2438	Suspended
0.6772	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6234	Discontinued
0.6763	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5177	Phase 3
0.6752	Remote Similarity	NPD3645	Discontinued
0.675	Remote Similarity	NPD5713	Approved
0.6741	Remote Similarity	NPD3021	Approved
0.6741	Remote Similarity	NPD3022	Approved
0.6738	Remote Similarity	NPD3443	Approved
0.6738	Remote Similarity	NPD4093	Discontinued
0.6738	Remote Similarity	NPD3445	Approved
0.6738	Remote Similarity	NPD3444	Approved
0.6735	Remote Similarity	NPD2605	Approved
0.6735	Remote Similarity	NPD2606	Approved
0.6732	Remote Similarity	NPD2346	Discontinued
0.6719	Remote Similarity	NPD2859	Approved
0.6719	Remote Similarity	NPD2860	Approved
0.6715	Remote Similarity	NPD1138	Approved
0.6713	Remote Similarity	NPD3705	Approved
0.6712	Remote Similarity	NPD3690	Phase 2
0.6712	Remote Similarity	NPD3691	Phase 2
0.6711	Remote Similarity	NPD839	Approved
0.6711	Remote Similarity	NPD840	Approved
0.6709	Remote Similarity	NPD4319	Phase 2
0.669	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6516	Phase 2
0.669	Remote Similarity	NPD1751	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