NPASS Compound

Structure

CID261896 OpenBabel06191716062D 43 49 0 0 1 0 0 0 0 0999 V2000 -5.5707 1.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7075 -0.4087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2686 -2.0466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3303 -2.5995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1155 -1.7135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6531 -0.6621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2142 -2.2999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1813 -3.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6270 -2.5483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7229 2.0983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7229 0.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6549 -1.9632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4651 1.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8404 -2.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 1.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4185 0.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5707 0.6299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0152 -1.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1369 -1.7392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9065 -1.6077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1599 -3.4086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1059 -2.5510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6304 2.0816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8751 0.6299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4395 0.5914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9384 -1.2787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8751 1.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1240 -1.7698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7444 0.6358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1240 -0.5942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0273 0.1404 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6729 -1.1820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5791 0.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3506 -0.8276 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3746 -0.9045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2664 0.6299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8521 -1.8611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6714 -4.2433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7313 -3.4554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6560 3.0602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0273 2.0983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0946 -1.6420 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 10 2 0 0 0 0 1 17 1 0 0 0 0 2 6 1 0 0 0 0 2 18 2 0 0 0 0 3 7 2 0 0 0 0 3 18 1 0 0 0 0 4 8 1 0 0 0 0 4 19 2 0 0 0 0 5 9 2 0 0 0 0 5 19 1 0 0 0 0 6 20 2 0 0 0 0 7 20 1 0 0 0 0 8 21 2 0 0 0 0 9 21 1 0 0 0 0 10 27 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 22 2 0 0 0 0 12 26 1 0 0 0 0 13 23 2 0 0 0 0 13 25 1 0 0 0 0 14 22 1 0 0 0 0 14 28 2 0 0 0 0 15 23 1 0 0 0 0 15 29 2 0 0 0 0 16 17 1 0 0 0 0 16 36 2 0 0 0 0 20 37 1 0 0 0 0 21 38 1 0 0 0 0 22 39 1 0 0 0 0 23 40 1 0 0 0 0 24 27 2 0 0 0 0 25 31 1 0 0 0 0 25 33 2 0 0 0 0 26 32 2 0 0 0 0 27 41 1 0 0 0 0 28 32 1 0 0 0 0 28 42 1 0 0 0 0 29 33 1 0 0 0 0 29 43 1 0 0 0 0 30 18 1 6 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 31 24 1 1 0 0 0 33 34 1 0 0 0 0 34 26 1 1 0 0 0 34 35 1 0 0 0 0 35 19 1 6 0 0 0 35 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.16
Volume:	582.159
LogP:	5.476
LogD:	3.346
LogS:	-3.996
# Rotatable Bonds:	4
TPSA:	147.68
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.138
Synthetic Accessibility Score:	4.247
Fsp3:	0.114
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.809
MDCK Permeability:	5.967443485133117e-06
Pgp-inhibitor:	0.236
Pgp-substrate:	0.131
Human Intestinal Absorption (HIA):	0.73
20% Bioavailability (F20%):	0.293
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	95.33574676513672%
Volume Distribution (VD):	0.64
Pgp-substrate:	3.1805217266082764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.227
CYP1A2-substrate:	0.517
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.994
CYP2D6-inhibitor:	0.268
CYP2D6-substrate:	0.573
CYP3A4-inhibitor:	0.485
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	8.943
Half-life (T1/2):	0.422

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.331
Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.928
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.912
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC261896

Natural Product ID:	NPC261896
*Common Name:**	Vitisinol B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LIOBMRCYNQGSIE-KLSCSJJOSA-N
Standard InCHI:	InChI=1S/C35H26O8/c36-16-17-1-10-27(41)24(11-17)31-25-13-23(40)15-29-33(25)34(35(43-29)19-4-8-21(38)9-5-19)26-12-22(39)14-28(42)32(26)30(31)18-2-6-20(37)7-3-18/h1-16,30-31,34-35,37-42H/t30-,31+,34+,35-/m1/s1
SMILES:	c1cc(c(cc1C=O)[C@H]1c2cc(cc3c2[C@H](c2cc(cc(c2[C@@H]1c1ccc(cc1)O)O)O)[C@@H](c1ccc(cc1)O)O3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443866
PubChem CID:	11353654
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843586]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11076554]
NPO11304	Vitis thunbergii	Species	Vitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15730246]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	red sea	n.a.	PMID[16180827]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[17190441]
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	Subaerial Parts	n.a.	n.a.	PMID[30207720]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572416]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778242]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461648]
NPO6028	Laurencia pinnatifida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5899	Ainsliaea uniflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10086	Scrophularia scorodonia	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9038	Aconitum burnatii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4980	Lycopodium erythraeum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12049	Lecania gerlachei	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1276	Thonningia sanguinea	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10313	Plantago arborescens	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11941	Helleborus serbicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16596	Dysoxylum schiffneri	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20597	Phascolion strombus	Species	Phascolionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO222	Phebalium drummondii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8519	Garcinia andamanica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11304	Vitis thunbergii	Species	Vitaceae	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
EC50	1
IC50	2

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[450693]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7800.0	nM	PMID[450693]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	3600.0	nM	PMID[450693]

☑ 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 NPC261896 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	427
0.1-0.2	1826
0.2-0.3	3718
0.3-0.4	10131
0.4-0.5	8428
0.5-0.6	3683
0.6-0.7	6024
0.7-0.8	6971
0.8-0.85	1312
0.85-0.9	166
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC301256
0.9062	High Similarity	NPC312273
0.9006	High Similarity	NPC473012
0.8951	High Similarity	NPC473009
0.8938	High Similarity	NPC195167
0.8903	High Similarity	NPC77903
0.8903	High Similarity	NPC17101
0.8896	High Similarity	NPC473010
0.8896	High Similarity	NPC474591
0.8889	High Similarity	NPC473011
0.8882	High Similarity	NPC226462
0.8882	High Similarity	NPC98023
0.8882	High Similarity	NPC292863
0.8882	High Similarity	NPC184326
0.8827	High Similarity	NPC18380
0.8827	High Similarity	NPC90822
0.8827	High Similarity	NPC137232
0.882	High Similarity	NPC15815
0.882	High Similarity	NPC18699
0.882	High Similarity	NPC55443
0.882	High Similarity	NPC105584
0.8805	High Similarity	NPC121568
0.8765	High Similarity	NPC42965
0.8765	High Similarity	NPC195136
0.8758	High Similarity	NPC208258
0.8758	High Similarity	NPC1796
0.8758	High Similarity	NPC257166
0.875	High Similarity	NPC300657
0.875	High Similarity	NPC79375
0.875	High Similarity	NPC254351
0.875	High Similarity	NPC37253
0.8742	High Similarity	NPC115601
0.8742	High Similarity	NPC208011
0.8742	High Similarity	NPC78324
0.8742	High Similarity	NPC39154
0.8727	High Similarity	NPC251336
0.872	High Similarity	NPC290160
0.8718	High Similarity	NPC111134
0.8704	High Similarity	NPC51247
0.8696	High Similarity	NPC69531
0.8696	High Similarity	NPC32867
0.8683	High Similarity	NPC180768
0.8667	High Similarity	NPC469664
0.8659	High Similarity	NPC477239
0.8659	High Similarity	NPC15374
0.8659	High Similarity	NPC3448
0.8654	High Similarity	NPC471473
0.8654	High Similarity	NPC471524
0.8654	High Similarity	NPC471523
0.865	High Similarity	NPC121647
0.8642	High Similarity	NPC475184
0.8642	High Similarity	NPC322459
0.8642	High Similarity	NPC324358
0.8642	High Similarity	NPC323627
0.8642	High Similarity	NPC318527
0.8634	High Similarity	NPC134171
0.8634	High Similarity	NPC182555
0.8634	High Similarity	NPC66441
0.8634	High Similarity	NPC300668
0.8625	High Similarity	NPC174086
0.8625	High Similarity	NPC43345
0.8614	High Similarity	NPC43065
0.8608	High Similarity	NPC35150
0.8608	High Similarity	NPC148516
0.8608	High Similarity	NPC180605
0.8608	High Similarity	NPC107862
0.8608	High Similarity	NPC177172
0.8608	High Similarity	NPC122894
0.8608	High Similarity	NPC122980
0.8608	High Similarity	NPC106328
0.8606	High Similarity	NPC38591
0.8598	High Similarity	NPC189552
0.8598	High Similarity	NPC273467
0.8589	High Similarity	NPC295090
0.858	High Similarity	NPC54830
0.858	High Similarity	NPC98583
0.858	High Similarity	NPC309648
0.858	High Similarity	NPC56049
0.8571	High Similarity	NPC324447
0.8563	High Similarity	NPC286230
0.8563	High Similarity	NPC253730
0.8562	High Similarity	NPC476553
0.8562	High Similarity	NPC476552
0.8562	High Similarity	NPC178484
0.8562	High Similarity	NPC476551
0.8554	High Similarity	NPC169471
0.8553	High Similarity	NPC3642
0.8553	High Similarity	NPC132345
0.8538	High Similarity	NPC475783
0.8537	High Similarity	NPC312993
0.8537	High Similarity	NPC472060
0.8537	High Similarity	NPC186325
0.8537	High Similarity	NPC472052
0.8537	High Similarity	NPC470342
0.8528	High Similarity	NPC271741
0.8528	High Similarity	NPC287789
0.8521	High Similarity	NPC477529
0.8521	High Similarity	NPC100251
0.8521	High Similarity	NPC65333
0.8519	High Similarity	NPC100049
0.8519	High Similarity	NPC201227
0.8519	High Similarity	NPC52611
0.8519	High Similarity	NPC150908
0.8519	High Similarity	NPC258474
0.8519	High Similarity	NPC205026
0.8519	High Similarity	NPC215203
0.8519	High Similarity	NPC158027
0.8519	High Similarity	NPC186227
0.8519	High Similarity	NPC14606
0.8519	High Similarity	NPC159707
0.8519	High Similarity	NPC265624
0.8519	High Similarity	NPC121649
0.8519	High Similarity	NPC248739
0.8512	High Similarity	NPC300307
0.8503	High Similarity	NPC224851
0.8503	High Similarity	NPC320741
0.8503	High Similarity	NPC477835
0.8503	High Similarity	NPC171985
0.85	High Similarity	NPC233886
0.85	High Similarity	NPC105073
0.85	High Similarity	NPC224528
0.8494	Intermediate Similarity	NPC45943
0.8494	Intermediate Similarity	NPC100849
0.8491	Intermediate Similarity	NPC152233
0.8481	Intermediate Similarity	NPC231712
0.8481	Intermediate Similarity	NPC242774
0.8481	Intermediate Similarity	NPC224921
0.8481	Intermediate Similarity	NPC133209
0.8481	Intermediate Similarity	NPC237546
0.8481	Intermediate Similarity	NPC73320
0.8481	Intermediate Similarity	NPC112819
0.8481	Intermediate Similarity	NPC6702
0.8476	Intermediate Similarity	NPC51760
0.8476	Intermediate Similarity	NPC177650
0.8466	Intermediate Similarity	NPC61112
0.8466	Intermediate Similarity	NPC198489
0.8457	Intermediate Similarity	NPC290830
0.8457	Intermediate Similarity	NPC71061
0.8457	Intermediate Similarity	NPC72425
0.8457	Intermediate Similarity	NPC122365
0.8457	Intermediate Similarity	NPC303485
0.8457	Intermediate Similarity	NPC194593
0.8447	Intermediate Similarity	NPC138299
0.8447	Intermediate Similarity	NPC67322
0.8447	Intermediate Similarity	NPC317715
0.8447	Intermediate Similarity	NPC204561
0.8447	Intermediate Similarity	NPC148945
0.8447	Intermediate Similarity	NPC309512
0.8447	Intermediate Similarity	NPC222713
0.8447	Intermediate Similarity	NPC316960
0.8447	Intermediate Similarity	NPC111112
0.8447	Intermediate Similarity	NPC78835
0.8438	Intermediate Similarity	NPC291746
0.8438	Intermediate Similarity	NPC288840
0.8434	Intermediate Similarity	NPC149389
0.8434	Intermediate Similarity	NPC477528
0.8428	Intermediate Similarity	NPC475348
0.8428	Intermediate Similarity	NPC261271
0.8424	Intermediate Similarity	NPC472618
0.8418	Intermediate Similarity	NPC470135
0.8418	Intermediate Similarity	NPC39045
0.8418	Intermediate Similarity	NPC470136
0.8415	Intermediate Similarity	NPC272196
0.8412	Intermediate Similarity	NPC477836
0.8412	Intermediate Similarity	NPC4200
0.8405	Intermediate Similarity	NPC148938
0.8405	Intermediate Similarity	NPC66508
0.8405	Intermediate Similarity	NPC226656
0.8402	Intermediate Similarity	NPC107627
0.8402	Intermediate Similarity	NPC53252
0.8395	Intermediate Similarity	NPC87708
0.8395	Intermediate Similarity	NPC154683
0.8395	Intermediate Similarity	NPC40356
0.8393	Intermediate Similarity	NPC82330
0.8391	Intermediate Similarity	NPC150977
0.8387	Intermediate Similarity	NPC174787
0.8387	Intermediate Similarity	NPC182509
0.8387	Intermediate Similarity	NPC213607
0.8383	Intermediate Similarity	NPC63438
0.8375	Intermediate Similarity	NPC168085
0.8373	Intermediate Similarity	NPC92589
0.8373	Intermediate Similarity	NPC175513
0.8373	Intermediate Similarity	NPC469889
0.8373	Intermediate Similarity	NPC216916
0.8366	Intermediate Similarity	NPC11727
0.8366	Intermediate Similarity	NPC125579
0.8366	Intermediate Similarity	NPC15109
0.8365	Intermediate Similarity	NPC473078
0.8365	Intermediate Similarity	NPC228779
0.8365	Intermediate Similarity	NPC470131
0.8365	Intermediate Similarity	NPC470134
0.8365	Intermediate Similarity	NPC109183
0.8365	Intermediate Similarity	NPC470132
0.8365	Intermediate Similarity	NPC470133
0.8364	Intermediate Similarity	NPC472617
0.8364	Intermediate Similarity	NPC226287
0.8364	Intermediate Similarity	NPC324736
0.8364	Intermediate Similarity	NPC90497
0.8364	Intermediate Similarity	NPC123544
0.8364	Intermediate Similarity	NPC472877

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 NPC261896 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1004
0.2-0.3	1566
0.3-0.4	2647
0.4-0.5	1903
0.5-0.6	1041
0.6-0.7	427
0.7-0.8	141
0.8-0.85	18
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8598	High Similarity	NPD6959	Discontinued
0.8519	High Similarity	NPD8443	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7768	Phase 2
0.8187	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7411	Suspended
0.8092	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3749	Approved
0.8081	Intermediate Similarity	NPD5844	Phase 1
0.805	Intermediate Similarity	NPD3750	Approved
0.8049	Intermediate Similarity	NPD4380	Phase 2
0.8038	Intermediate Similarity	NPD1549	Phase 2
0.8012	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6166	Phase 2
0.7901	Intermediate Similarity	NPD7390	Discontinued
0.7882	Intermediate Similarity	NPD5494	Approved
0.7879	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7075	Discontinued
0.7853	Intermediate Similarity	NPD8312	Approved
0.7853	Intermediate Similarity	NPD8313	Approved
0.7848	Intermediate Similarity	NPD1510	Phase 2
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7806	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2796	Approved
0.7791	Intermediate Similarity	NPD6232	Discontinued
0.7765	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7473	Discontinued
0.7744	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD2532	Approved
0.7744	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2534	Approved
0.7738	Intermediate Similarity	NPD1934	Approved
0.7736	Intermediate Similarity	NPD3748	Approved
0.7716	Intermediate Similarity	NPD7003	Approved
0.7714	Intermediate Similarity	NPD3818	Discontinued
0.7706	Intermediate Similarity	NPD3882	Suspended
0.7702	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7229	Phase 3
0.7677	Intermediate Similarity	NPD4908	Phase 1
0.767	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6801	Discontinued
0.763	Intermediate Similarity	NPD7199	Phase 2
0.7595	Intermediate Similarity	NPD1240	Approved
0.759	Intermediate Similarity	NPD6273	Approved
0.7588	Intermediate Similarity	NPD1465	Phase 2
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD1511	Approved
0.7543	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7074	Phase 3
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7177	Discontinued
0.75	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD1512	Approved
0.7485	Intermediate Similarity	NPD2801	Approved
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7472	Intermediate Similarity	NPD7054	Approved
0.7469	Intermediate Similarity	NPD5405	Approved
0.7469	Intermediate Similarity	NPD6099	Approved
0.7469	Intermediate Similarity	NPD5406	Approved
0.7469	Intermediate Similarity	NPD6100	Approved
0.7469	Intermediate Similarity	NPD5404	Approved
0.7469	Intermediate Similarity	NPD5408	Approved
0.7468	Intermediate Similarity	NPD3764	Approved
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3226	Approved
0.7456	Intermediate Similarity	NPD7458	Discontinued
0.744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD920	Approved
0.7439	Intermediate Similarity	NPD2800	Approved
0.743	Intermediate Similarity	NPD7472	Approved
0.7427	Intermediate Similarity	NPD37	Approved
0.7425	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6234	Discontinued
0.7407	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7808	Phase 3
0.7403	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4965	Approved
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7394	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6797	Phase 2
0.7377	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6799	Approved
0.7362	Intermediate Similarity	NPD2935	Discontinued
0.7348	Intermediate Similarity	NPD7251	Discontinued
0.7341	Intermediate Similarity	NPD5402	Approved
0.7341	Intermediate Similarity	NPD3817	Phase 2
0.7338	Intermediate Similarity	NPD1610	Phase 2
0.7337	Intermediate Similarity	NPD5403	Approved
0.7321	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7228	Approved
0.7317	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2344	Approved
0.7314	Intermediate Similarity	NPD919	Approved
0.731	Intermediate Similarity	NPD6599	Discontinued
0.7301	Intermediate Similarity	NPD2799	Discontinued
0.7296	Intermediate Similarity	NPD4625	Phase 3
0.7283	Intermediate Similarity	NPD5760	Phase 2
0.7283	Intermediate Similarity	NPD5761	Phase 2
0.7247	Intermediate Similarity	NPD3926	Phase 2
0.7245	Intermediate Similarity	NPD8151	Discontinued
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7241	Intermediate Similarity	NPD4288	Approved
0.7232	Intermediate Similarity	NPD1247	Approved
0.7229	Intermediate Similarity	NPD1243	Approved
0.7222	Intermediate Similarity	NPD3751	Discontinued
0.7219	Intermediate Similarity	NPD5401	Approved
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7213	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5953	Discontinued
0.7191	Intermediate Similarity	NPD5710	Approved
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.7191	Intermediate Similarity	NPD5711	Approved
0.7178	Intermediate Similarity	NPD6651	Approved
0.717	Intermediate Similarity	NPD2861	Phase 2
0.7166	Intermediate Similarity	NPD4287	Approved
0.716	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2309	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.712	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5124	Phase 1
0.7117	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2346	Discontinued
0.7098	Intermediate Similarity	NPD6779	Approved
0.7098	Intermediate Similarity	NPD6777	Approved
0.7098	Intermediate Similarity	NPD6782	Approved
0.7098	Intermediate Similarity	NPD6781	Approved
0.7098	Intermediate Similarity	NPD6776	Approved
0.7098	Intermediate Similarity	NPD6780	Approved
0.7098	Intermediate Similarity	NPD6778	Approved
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.7077	Intermediate Similarity	NPD7698	Approved
0.7077	Intermediate Similarity	NPD7697	Approved
0.7077	Intermediate Similarity	NPD7696	Phase 3
0.707	Intermediate Similarity	NPD1608	Approved
0.7069	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8150	Discontinued
0.7055	Intermediate Similarity	NPD4060	Phase 1
0.7055	Intermediate Similarity	NPD1613	Approved
0.7055	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2797	Approved
0.7037	Intermediate Similarity	NPD3268	Approved
0.7035	Intermediate Similarity	NPD7427	Discontinued
0.7016	Intermediate Similarity	NPD4360	Phase 2
0.7016	Intermediate Similarity	NPD4363	Phase 3
0.701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7783	Phase 2
0.6995	Remote Similarity	NPD7286	Phase 2
0.699	Remote Similarity	NPD7435	Discontinued
0.6988	Remote Similarity	NPD7033	Discontinued
0.6982	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8166	Discontinued
0.6979	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4361	Phase 2
0.6973	Remote Similarity	NPD7240	Approved
0.6973	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6971	Discontinued
0.6951	Remote Similarity	NPD943	Approved
0.6946	Remote Similarity	NPD4477	Approved
0.6946	Remote Similarity	NPD4476	Approved
0.6937	Remote Similarity	NPD1203	Approved
0.6937	Remote Similarity	NPD1470	Approved
0.6935	Remote Similarity	NPD7701	Phase 2
0.6933	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6798	Discontinued
0.6933	Remote Similarity	NPD2313	Discontinued
0.6918	Remote Similarity	NPD4749	Approved
0.6915	Remote Similarity	NPD7801	Approved
0.6914	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6832	Phase 2
0.6909	Remote Similarity	NPD230	Phase 1
0.6909	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6004	Phase 3
0.6905	Remote Similarity	NPD6005	Phase 3
0.6905	Remote Similarity	NPD6002	Phase 3
0.6899	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1201	Approved
0.6886	Remote Similarity	NPD4308	Phase 3
0.6882	Remote Similarity	NPD7685	Pre-registration
0.6879	Remote Similarity	NPD17	Approved
0.6875	Remote Similarity	NPD1283	Approved
0.6875	Remote Similarity	NPD3225	Approved
0.6875	Remote Similarity	NPD1876	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