NPASS Compound

Structure

CID38159 OpenBabel06191715372D 36 40 0 0 1 0 0 0 0 0999 V2000 -1.5109 -3.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6180 4.3501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9875 -0.4108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0877 2.3573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0335 0.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2501 0.2423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1370 -2.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7373 4.0602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2153 -2.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0459 4.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1586 -1.8759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1652 4.3881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0803 -1.7755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0241 3.4804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4541 -0.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6673 2.8627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9063 -0.1790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2887 1.0474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4309 -0.1809 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1448 0.8524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0515 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6082 0.6953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3721 0.2827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6658 0.5516 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1199 0.4395 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3761 0.5516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1793 1.1896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6658 -0.0499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3758 -0.8266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5480 3.1526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8128 0.8534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5299 0.7958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4993 2.0598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8349 -0.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7428 1.2865 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 9 2 0 0 0 0 8 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 14 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 29 2 0 0 0 0 16 18 1 0 0 0 0 16 30 2 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 6 0 0 0 19 25 1 0 0 0 0 20 24 1 6 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 0 0 0 0 23 27 1 1 0 0 0 24 28 1 1 0 0 0 25 28 1 6 0 0 0 25 35 1 0 0 0 0 26 27 1 6 0 0 0 26 36 1 0 0 0 0 27 33 1 1 0 0 0 27 35 1 0 0 0 0 28 34 1 1 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.21
Volume:	499.292
LogP:	3.392
LogD:	1.454
LogS:	-4.482
# Rotatable Bonds:	6
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	7.412
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.442
MDCK Permeability:	1.7561213098815642e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.208
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.253

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	75.4636459350586%
Volume Distribution (VD):	2.079
Pgp-substrate:	10.546907424926758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.151
CYP3A4-substrate:	0.935

ADMET: Excretion

Clearance (CL):	5.977
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.545
Drug-inuced Liver Injury (DILI):	0.535
AMES Toxicity:	0.235
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.924
Carcinogencity:	0.952
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC38159

Natural Product ID:	NPC38159
*Common Name:**	Trichodimerol
IUPAC Name:	n.a.
Synonyms:	Trichodimerol
Standard InCHIKey:	VATYWOIGKMMCMM-OXGNLDDNSA-N
Standard InCHI:	InChI=1S/C28H32O8/c1-7-9-11-13-15(29)17-19-23(3)22(32)18(16(30)14-12-10-8-2)20-24(4,21(17)31)28(34)25(19,5)35-27(23,33)26(20,6)36-28/h7-14,19-20,31-34H,1-6H3/b9-7+,10-8+,13-11+,14-12+/t19-,20-,23-,24-,25+,26+,27-,28-/m1/s1
SMILES:	C/C=C/C=C/C(=O)C1=C(O)[C@@]2(C)[C@H]3C(=C([C@]4([C@@H]1[C@]1([C@]2(O)O[C@@]3([C@@]4(O1)O)C)C)C)O)C(=O)/C=C/C=C/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1643641
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO28966	Trichoderma longibrachiatum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429993]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21381678]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22118684]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33089690]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8626236]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO28966	Trichoderma longibrachiatum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO28966	Trichoderma longibrachiatum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	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
IC50	4
MIC	1

Activity Type	# Activity
Cell Line	3
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	74400.0	nM	PMID[530546]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	28500.0	nM	PMID[530546]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	16500.0	nM	PMID[530546]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	6290.0	nM	PMID[530546]
NPT2	Others	Unspecified		IC50	=	47800.0	nM	PMID[530546]

☑ 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 NPC38159 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	240
0.1-0.2	1218
0.2-0.3	4991
0.3-0.4	9737
0.4-0.5	15057
0.5-0.6	8620
0.6-0.7	2738
0.7-0.8	90
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7913	Intermediate Similarity	NPC471204
0.7881	Intermediate Similarity	NPC469488
0.7845	Intermediate Similarity	NPC247069
0.7815	Intermediate Similarity	NPC48692
0.7807	Intermediate Similarity	NPC474567
0.7805	Intermediate Similarity	NPC473888
0.7797	Intermediate Similarity	NPC204552
0.7797	Intermediate Similarity	NPC188667
0.7788	Intermediate Similarity	NPC272576
0.7788	Intermediate Similarity	NPC473288
0.7787	Intermediate Similarity	NPC181999
0.7778	Intermediate Similarity	NPC328374
0.7778	Intermediate Similarity	NPC40632
0.7778	Intermediate Similarity	NPC235539
0.7778	Intermediate Similarity	NPC96312
0.7778	Intermediate Similarity	NPC251236
0.7778	Intermediate Similarity	NPC152199
0.7778	Intermediate Similarity	NPC134869
0.776	Intermediate Similarity	NPC102316
0.7759	Intermediate Similarity	NPC49451
0.775	Intermediate Similarity	NPC102822
0.775	Intermediate Similarity	NPC477046
0.7742	Intermediate Similarity	NPC264192
0.7712	Intermediate Similarity	NPC122033
0.7712	Intermediate Similarity	NPC470854
0.7712	Intermediate Similarity	NPC97908
0.7712	Intermediate Similarity	NPC27999
0.7712	Intermediate Similarity	NPC477116
0.7712	Intermediate Similarity	NPC287343
0.7712	Intermediate Similarity	NPC474654
0.7692	Intermediate Similarity	NPC18547
0.7692	Intermediate Similarity	NPC474906
0.7692	Intermediate Similarity	NPC473798
0.7672	Intermediate Similarity	NPC11252
0.7672	Intermediate Similarity	NPC289312
0.7667	Intermediate Similarity	NPC112038
0.7652	Intermediate Similarity	NPC210005
0.7647	Intermediate Similarity	NPC234522
0.7647	Intermediate Similarity	NPC297179
0.7642	Intermediate Similarity	NPC93368
0.7642	Intermediate Similarity	NPC225049
0.7627	Intermediate Similarity	NPC302471
0.7627	Intermediate Similarity	NPC207217
0.7619	Intermediate Similarity	NPC100390
0.7619	Intermediate Similarity	NPC254614
0.7611	Intermediate Similarity	NPC471332
0.7611	Intermediate Similarity	NPC471333
0.7607	Intermediate Similarity	NPC255017
0.7589	Intermediate Similarity	NPC474575
0.7586	Intermediate Similarity	NPC201992
0.7586	Intermediate Similarity	NPC188738
0.7586	Intermediate Similarity	NPC471243
0.7583	Intermediate Similarity	NPC475775
0.7583	Intermediate Similarity	NPC470777
0.7583	Intermediate Similarity	NPC476529
0.7581	Intermediate Similarity	NPC305496
0.7563	Intermediate Similarity	NPC473968
0.7559	Intermediate Similarity	NPC168879
0.7545	Intermediate Similarity	NPC70733
0.7545	Intermediate Similarity	NPC56071
0.7544	Intermediate Similarity	NPC293512
0.7542	Intermediate Similarity	NPC471398
0.754	Intermediate Similarity	NPC251564
0.754	Intermediate Similarity	NPC475606
0.754	Intermediate Similarity	NPC477189
0.754	Intermediate Similarity	NPC475314
0.7523	Intermediate Similarity	NPC256230
0.7522	Intermediate Similarity	NPC65523
0.7521	Intermediate Similarity	NPC107338
0.7521	Intermediate Similarity	NPC174836
0.7521	Intermediate Similarity	NPC241192
0.7521	Intermediate Similarity	NPC90769
0.7521	Intermediate Similarity	NPC474516
0.7521	Intermediate Similarity	NPC472002
0.7521	Intermediate Similarity	NPC109607
0.7519	Intermediate Similarity	NPC243014
0.75	Intermediate Similarity	NPC176005
0.75	Intermediate Similarity	NPC17772
0.75	Intermediate Similarity	NPC106644
0.75	Intermediate Similarity	NPC242486
0.75	Intermediate Similarity	NPC15215
0.75	Intermediate Similarity	NPC5284
0.748	Intermediate Similarity	NPC474508
0.748	Intermediate Similarity	NPC33378
0.748	Intermediate Similarity	NPC6274
0.748	Intermediate Similarity	NPC473485
0.748	Intermediate Similarity	NPC227397
0.748	Intermediate Similarity	NPC254146
0.7478	Intermediate Similarity	NPC258323
0.7478	Intermediate Similarity	NPC94942
0.7459	Intermediate Similarity	NPC202051
0.7459	Intermediate Similarity	NPC42675
0.7458	Intermediate Similarity	NPC7921
0.7458	Intermediate Similarity	NPC293038
0.7458	Intermediate Similarity	NPC320118
0.7458	Intermediate Similarity	NPC51978
0.7458	Intermediate Similarity	NPC178981
0.7458	Intermediate Similarity	NPC194273
0.7458	Intermediate Similarity	NPC469454
0.7458	Intermediate Similarity	NPC471627
0.7458	Intermediate Similarity	NPC311592
0.7458	Intermediate Similarity	NPC208998
0.7458	Intermediate Similarity	NPC469496
0.7458	Intermediate Similarity	NPC75167
0.7458	Intermediate Similarity	NPC469463
0.7458	Intermediate Similarity	NPC62696
0.7458	Intermediate Similarity	NPC471173
0.7456	Intermediate Similarity	NPC96377
0.7456	Intermediate Similarity	NPC102352
0.7455	Intermediate Similarity	NPC278506
0.744	Intermediate Similarity	NPC152091
0.7438	Intermediate Similarity	NPC279143
0.7438	Intermediate Similarity	NPC161065
0.7438	Intermediate Similarity	NPC268958
0.7438	Intermediate Similarity	NPC473920
0.7436	Intermediate Similarity	NPC304180
0.7436	Intermediate Similarity	NPC474229
0.7436	Intermediate Similarity	NPC179798
0.7431	Intermediate Similarity	NPC108141
0.7419	Intermediate Similarity	NPC190846
0.7419	Intermediate Similarity	NPC277191
0.7419	Intermediate Similarity	NPC24651
0.7419	Intermediate Similarity	NPC470922
0.7417	Intermediate Similarity	NPC218970
0.7417	Intermediate Similarity	NPC23046
0.7414	Intermediate Similarity	NPC300026
0.7411	Intermediate Similarity	NPC477871
0.7411	Intermediate Similarity	NPC477870
0.7411	Intermediate Similarity	NPC476213
0.7411	Intermediate Similarity	NPC476246
0.7411	Intermediate Similarity	NPC181645
0.7411	Intermediate Similarity	NPC9878
0.7398	Intermediate Similarity	NPC222688
0.7395	Intermediate Similarity	NPC181145
0.7395	Intermediate Similarity	NPC102088
0.7395	Intermediate Similarity	NPC117712
0.7395	Intermediate Similarity	NPC243354
0.7391	Intermediate Similarity	NPC59530
0.7391	Intermediate Similarity	NPC3316
0.7391	Intermediate Similarity	NPC144854
0.7381	Intermediate Similarity	NPC473620
0.7381	Intermediate Similarity	NPC188291
0.7377	Intermediate Similarity	NPC478051
0.7377	Intermediate Similarity	NPC474585
0.7373	Intermediate Similarity	NPC269530
0.7373	Intermediate Similarity	NPC234042
0.7373	Intermediate Similarity	NPC205534
0.7373	Intermediate Similarity	NPC152117
0.7368	Intermediate Similarity	NPC40170
0.7368	Intermediate Similarity	NPC255309
0.7364	Intermediate Similarity	NPC100017
0.7364	Intermediate Similarity	NPC473548
0.7364	Intermediate Similarity	NPC475154
0.7364	Intermediate Similarity	NPC223356
0.7364	Intermediate Similarity	NPC475500
0.7364	Intermediate Similarity	NPC471137
0.7364	Intermediate Similarity	NPC182266
0.7364	Intermediate Similarity	NPC471136
0.736	Intermediate Similarity	NPC174367
0.736	Intermediate Similarity	NPC47113
0.736	Intermediate Similarity	NPC217901
0.7355	Intermediate Similarity	NPC284707
0.7355	Intermediate Similarity	NPC251310
0.7355	Intermediate Similarity	NPC318751
0.735	Intermediate Similarity	NPC127153
0.735	Intermediate Similarity	NPC470065
0.735	Intermediate Similarity	NPC286880
0.7345	Intermediate Similarity	NPC476126
0.7345	Intermediate Similarity	NPC476235
0.7345	Intermediate Similarity	NPC223834
0.7339	Intermediate Similarity	NPC258674
0.7339	Intermediate Similarity	NPC41129
0.7339	Intermediate Similarity	NPC1980
0.7339	Intermediate Similarity	NPC91693
0.7339	Intermediate Similarity	NPC238005
0.7339	Intermediate Similarity	NPC473979
0.7339	Intermediate Similarity	NPC141196
0.7339	Intermediate Similarity	NPC18945
0.7339	Intermediate Similarity	NPC265557
0.7339	Intermediate Similarity	NPC105926
0.7333	Intermediate Similarity	NPC16081
0.7333	Intermediate Similarity	NPC173686
0.7333	Intermediate Similarity	NPC259306
0.7333	Intermediate Similarity	NPC179626
0.7333	Intermediate Similarity	NPC243981
0.7333	Intermediate Similarity	NPC474734
0.7333	Intermediate Similarity	NPC470628
0.7333	Intermediate Similarity	NPC473126
0.7333	Intermediate Similarity	NPC474046
0.7328	Intermediate Similarity	NPC192813
0.7328	Intermediate Similarity	NPC277017
0.7328	Intermediate Similarity	NPC293850
0.7328	Intermediate Similarity	NPC168883
0.7328	Intermediate Similarity	NPC154608
0.7328	Intermediate Similarity	NPC29827
0.7323	Intermediate Similarity	NPC231529
0.7323	Intermediate Similarity	NPC162495
0.7317	Intermediate Similarity	NPC310511
0.7317	Intermediate Similarity	NPC275675
0.7311	Intermediate Similarity	NPC56448

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 NPC38159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1653
0.2-0.3	4065
0.3-0.4	2245
0.4-0.5	614
0.5-0.6	298
0.6-0.7	60
0.7-0.8	0
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
0.7377	Intermediate Similarity	NPD6054	Approved
0.7258	Intermediate Similarity	NPD6370	Approved
0.7177	Intermediate Similarity	NPD6016	Approved
0.7177	Intermediate Similarity	NPD6015	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.712	Intermediate Similarity	NPD5988	Approved
0.7097	Intermediate Similarity	NPD6059	Approved
0.7094	Intermediate Similarity	NPD6412	Phase 2
0.7087	Intermediate Similarity	NPD6616	Approved
0.7034	Intermediate Similarity	NPD6686	Approved
0.7031	Intermediate Similarity	NPD7078	Approved
0.7027	Intermediate Similarity	NPD5282	Discontinued
0.7	Intermediate Similarity	NPD6411	Approved
0.6977	Remote Similarity	NPD7736	Approved
0.696	Remote Similarity	NPD6319	Approved
0.6942	Remote Similarity	NPD8297	Approved
0.6942	Remote Similarity	NPD6882	Approved
0.6929	Remote Similarity	NPD8328	Phase 3
0.6905	Remote Similarity	NPD8515	Approved
0.6905	Remote Similarity	NPD8513	Phase 3
0.6905	Remote Similarity	NPD8516	Approved
0.6905	Remote Similarity	NPD8517	Approved
0.6885	Remote Similarity	NPD4632	Approved
0.6864	Remote Similarity	NPD6008	Approved
0.686	Remote Similarity	NPD6650	Approved
0.686	Remote Similarity	NPD6649	Approved
0.6855	Remote Similarity	NPD6009	Approved
0.6847	Remote Similarity	NPD5284	Approved
0.6847	Remote Similarity	NPD5281	Approved
0.6833	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7507	Approved
0.6818	Remote Similarity	NPD7260	Phase 2
0.6818	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6101	Approved
0.6794	Remote Similarity	NPD7319	Approved
0.6789	Remote Similarity	NPD3573	Approved
0.6769	Remote Similarity	NPD8293	Discontinued
0.6757	Remote Similarity	NPD5207	Approved
0.675	Remote Similarity	NPD6899	Approved
0.675	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6881	Approved
0.6694	Remote Similarity	NPD6372	Approved
0.6694	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6642	Remote Similarity	NPD6845	Suspended
0.6641	Remote Similarity	NPD7503	Approved
0.6641	Remote Similarity	NPD8074	Phase 3
0.6639	Remote Similarity	NPD7102	Approved
0.6639	Remote Similarity	NPD4634	Approved
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7290	Approved
0.6639	Remote Similarity	NPD6883	Approved
0.6637	Remote Similarity	NPD5778	Approved
0.6637	Remote Similarity	NPD5779	Approved
0.6612	Remote Similarity	NPD7320	Approved
0.6604	Remote Similarity	NPD4695	Discontinued
0.6591	Remote Similarity	NPD6033	Approved
0.6587	Remote Similarity	NPD7115	Discovery
0.6587	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8130	Phase 1
0.6585	Remote Similarity	NPD6847	Approved
0.6585	Remote Similarity	NPD6869	Approved
0.6585	Remote Similarity	NPD6617	Approved
0.6583	Remote Similarity	NPD7128	Approved
0.6583	Remote Similarity	NPD6402	Approved
0.6583	Remote Similarity	NPD6675	Approved
0.6583	Remote Similarity	NPD5739	Approved
0.6581	Remote Similarity	NPD5285	Approved
0.6581	Remote Similarity	NPD5286	Approved
0.6581	Remote Similarity	NPD4696	Approved
0.6557	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6012	Approved
0.6557	Remote Similarity	NPD6013	Approved
0.6557	Remote Similarity	NPD6014	Approved
0.6549	Remote Similarity	NPD6079	Approved
0.6538	Remote Similarity	NPD7604	Phase 2
0.6535	Remote Similarity	NPD7327	Approved
0.6535	Remote Similarity	NPD7328	Approved
0.6518	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5983	Phase 2
0.6496	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6399	Phase 3
0.6484	Remote Similarity	NPD7516	Approved
0.6475	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD4633	Approved
0.6471	Remote Similarity	NPD5225	Approved
0.6471	Remote Similarity	NPD5211	Phase 2
0.6471	Remote Similarity	NPD5224	Approved
0.6471	Remote Similarity	NPD5226	Approved
0.6452	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6336	Discontinued
0.6429	Remote Similarity	NPD4518	Approved
0.6417	Remote Similarity	NPD5174	Approved
0.6417	Remote Similarity	NPD5175	Approved
0.6412	Remote Similarity	NPD6067	Discontinued
0.641	Remote Similarity	NPD7902	Approved
0.641	Remote Similarity	NPD4755	Approved
0.6406	Remote Similarity	NPD7641	Discontinued
0.6404	Remote Similarity	NPD7983	Approved
0.6404	Remote Similarity	NPD6050	Approved
0.6404	Remote Similarity	NPD5694	Approved
0.64	Remote Similarity	NPD6053	Discontinued
0.6396	Remote Similarity	NPD5280	Approved
0.6396	Remote Similarity	NPD5690	Phase 2
0.6396	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4694	Approved
0.6393	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5701	Approved
0.6387	Remote Similarity	NPD5223	Approved
0.6379	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5695	Phase 3
0.6379	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5328	Approved
0.6364	Remote Similarity	NPD5141	Approved
0.6356	Remote Similarity	NPD4225	Approved
0.6341	Remote Similarity	NPD4730	Approved
0.6341	Remote Similarity	NPD4729	Approved
0.6325	Remote Similarity	NPD5221	Approved
0.6325	Remote Similarity	NPD5222	Approved
0.6325	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5692	Phase 3
0.6316	Remote Similarity	NPD46	Approved
0.6316	Remote Similarity	NPD6698	Approved
0.6303	Remote Similarity	NPD4700	Approved
0.6303	Remote Similarity	NPD6648	Approved
0.6293	Remote Similarity	NPD7748	Approved
0.6271	Remote Similarity	NPD6083	Phase 2
0.6271	Remote Similarity	NPD6084	Phase 2
0.6271	Remote Similarity	NPD5173	Approved
0.626	Remote Similarity	NPD8033	Approved
0.626	Remote Similarity	NPD8335	Approved
0.626	Remote Similarity	NPD8296	Approved
0.626	Remote Similarity	NPD8380	Approved
0.626	Remote Similarity	NPD6921	Approved
0.626	Remote Similarity	NPD8378	Approved
0.626	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD5956	Approved
0.625	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD3618	Phase 1
0.624	Remote Similarity	NPD5250	Approved
0.624	Remote Similarity	NPD5247	Approved
0.624	Remote Similarity	NPD5248	Approved
0.624	Remote Similarity	NPD6371	Approved
0.624	Remote Similarity	NPD5249	Phase 3
0.624	Remote Similarity	NPD5251	Approved
0.6239	Remote Similarity	NPD5210	Approved
0.6239	Remote Similarity	NPD4629	Approved
0.6231	Remote Similarity	NPD7101	Approved
0.6231	Remote Similarity	NPD7100	Approved
0.622	Remote Similarity	NPD8133	Approved
0.6218	Remote Similarity	NPD5696	Approved
0.619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4697	Phase 3
0.6183	Remote Similarity	NPD8377	Approved
0.6183	Remote Similarity	NPD8294	Approved
0.6182	Remote Similarity	NPD4223	Phase 3
0.6182	Remote Similarity	NPD4221	Approved
0.6179	Remote Similarity	NPD4767	Approved
0.6179	Remote Similarity	NPD4768	Approved
0.6174	Remote Similarity	NPD4096	Approved
0.6174	Remote Similarity	NPD7838	Discovery
0.6161	Remote Similarity	NPD5329	Approved
0.6154	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7900	Approved
0.6154	Remote Similarity	NPD6001	Approved
0.6147	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6274	Approved
0.6121	Remote Similarity	NPD7515	Phase 2
0.6106	Remote Similarity	NPD4623	Approved
0.6106	Remote Similarity	NPD4519	Discontinued
0.6099	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6673	Approved
0.6087	Remote Similarity	NPD4753	Phase 2
0.6087	Remote Similarity	NPD6080	Approved
0.6087	Remote Similarity	NPD6904	Approved
0.6083	Remote Similarity	NPD7638	Approved
0.608	Remote Similarity	NPD5128	Approved
0.6077	Remote Similarity	NPD6317	Approved
0.6071	Remote Similarity	NPD4786	Approved
0.6071	Remote Similarity	NPD4197	Approved
0.6068	Remote Similarity	NPD4202	Approved
0.6063	Remote Similarity	NPD5215	Approved
0.6063	Remote Similarity	NPD5216	Approved
0.6063	Remote Similarity	NPD5217	Approved
0.6053	Remote Similarity	NPD7524	Approved
0.605	Remote Similarity	NPD7839	Suspended
0.6043	Remote Similarity	NPD8338	Approved
0.6036	Remote Similarity	NPD3667	Approved
0.6033	Remote Similarity	NPD7640	Approved
0.6033	Remote Similarity	NPD7639	Approved
0.6031	Remote Similarity	NPD6313	Approved
0.6031	Remote Similarity	NPD6314	Approved
0.6016	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6903	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