NPASS Compound

Structure

CID111585 OpenBabel06191715462D 36 39 0 0 1 0 0 0 0 0999 V2000 -0.0791 -6.5967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4659 -5.9083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7339 1.6011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3867 2.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2638 2.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5397 -0.5250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6710 -4.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0972 -4.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2735 -3.2322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8470 1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6938 1.9546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 -0.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6930 -0.9774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2320 0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3859 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6920 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8462 -1.4660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4947 -5.8065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8045 1.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8473 -2.4420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8470 -1.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6932 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 1.4656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2323 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8185 -2.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3864 1.9541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5400 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9770 0.0000 C 0 0 1 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 -5.6011 0.3438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2160 -3.4358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3923 -1.7536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0786 1.9534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 7 31 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 20 2 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 18 32 1 0 0 0 0 19 31 1 0 0 0 0 21 33 2 0 0 0 0 21 36 1 0 0 0 0 22 11 1 6 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 31 1 6 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 6 0 0 0 27 29 1 0 0 0 0 27 36 1 1 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 30 6 1 6 0 0 0 31 32 1 6 0 0 0 32 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	552.417
LogP:	6.766
LogD:	4.986
LogS:	-5.483
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	4.727
Fsp3:	0.812
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:	-5.302
MDCK Permeability:	1.6811960449558683e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.323
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	94.0876235961914%
Volume Distribution (VD):	0.881
Pgp-substrate:	1.6078107357025146%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.214
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	2.999
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.768
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.375
Skin Sensitization:	0.427
Carcinogencity:	0.029
Eye Corrosion:	0.026
Eye Irritation:	0.346
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC111585

Natural Product ID:	NPC111585
*Common Name:**	Tsugaric Acid A
IUPAC Name:	(2R)-2-[(3R,5R,10S,13R,14R,17R)-3-acetyloxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:
Standard InCHIKey:	FIWGZIBLJWZUEA-CAHOJKFZSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-20(2)10-9-11-22(28(34)35)23-14-18-32(8)25-12-13-26-29(4,5)27(36-21(3)33)16-17-30(26,6)24(25)15-19-31(23,32)7/h10,22-23,26-27H,9,11-19H2,1-8H3,(H,34,35)/t22-,23-,26+,27-,30-,31-,32+/m1/s1
SMILES:	CC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)OC(=O)C)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497273
PubChem CID:	15292985
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785428]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[10785428]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21939217]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584403]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	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
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT550	Cell Line	T-24	Homo sapiens	ED50	=	3.1	ug ml-1	PMID[468982]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	6.8	ug ml-1	PMID[468982]

☑ 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 NPC111585 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	162
0.1-0.2	1021
0.2-0.3	4659
0.3-0.4	13821
0.4-0.5	8618
0.5-0.6	5802
0.6-0.7	5762
0.7-0.8	2462
0.8-0.85	281
0.85-0.9	83
0.9-0.95	21
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC148414
1.0	High Similarity	NPC175628
0.9882	High Similarity	NPC26888
0.9881	High Similarity	NPC474889
0.9765	High Similarity	NPC471896
0.9412	High Similarity	NPC233836
0.9412	High Similarity	NPC187376
0.9412	High Similarity	NPC159046
0.9326	High Similarity	NPC69548
0.9326	High Similarity	NPC184848
0.9302	High Similarity	NPC242864
0.9294	High Similarity	NPC28252
0.9294	High Similarity	NPC55309
0.9231	High Similarity	NPC477813
0.9222	High Similarity	NPC120708
0.9213	High Similarity	NPC159410
0.9205	High Similarity	NPC297265
0.9195	High Similarity	NPC77168
0.9195	High Similarity	NPC474704
0.9195	High Similarity	NPC475921
0.9195	High Similarity	NPC84271
0.9195	High Similarity	NPC102414
0.9186	High Similarity	NPC474684
0.9186	High Similarity	NPC142361
0.9111	High Similarity	NPC279974
0.9101	High Similarity	NPC470224
0.9091	High Similarity	NPC469400
0.907	High Similarity	NPC325594
0.9011	High Similarity	NPC327788
0.9	High Similarity	NPC469406
0.8989	High Similarity	NPC189520
0.8989	High Similarity	NPC23434
0.8977	High Similarity	NPC474570
0.8966	High Similarity	NPC167877
0.8901	High Similarity	NPC317586
0.8901	High Similarity	NPC162001
0.8901	High Similarity	NPC222845
0.8901	High Similarity	NPC473648
0.8901	High Similarity	NPC470016
0.8901	High Similarity	NPC45324
0.8889	High Similarity	NPC470375
0.8889	High Similarity	NPC141497
0.8889	High Similarity	NPC107674
0.8889	High Similarity	NPC170220
0.8889	High Similarity	NPC470376
0.8876	High Similarity	NPC20388
0.8876	High Similarity	NPC120840
0.8876	High Similarity	NPC113989
0.8864	High Similarity	NPC4309
0.8851	High Similarity	NPC264127
0.8851	High Similarity	NPC474970
0.8851	High Similarity	NPC94755
0.8851	High Similarity	NPC73038
0.8851	High Similarity	NPC155011
0.883	High Similarity	NPC473514
0.8817	High Similarity	NPC119036
0.8804	High Similarity	NPC173272
0.8791	High Similarity	NPC166906
0.8778	High Similarity	NPC77099
0.8778	High Similarity	NPC110657
0.8778	High Similarity	NPC60755
0.8778	High Similarity	NPC285184
0.8778	High Similarity	NPC212301
0.8778	High Similarity	NPC86266
0.8778	High Similarity	NPC470590
0.8764	High Similarity	NPC30522
0.8737	High Similarity	NPC473788
0.8737	High Similarity	NPC475558
0.8721	High Similarity	NPC471037
0.8706	High Similarity	NPC38350
0.8706	High Similarity	NPC201912
0.8706	High Similarity	NPC327002
0.8696	High Similarity	NPC469599
0.8696	High Similarity	NPC48330
0.869	High Similarity	NPC327674
0.8681	High Similarity	NPC86368
0.8681	High Similarity	NPC38232
0.8667	High Similarity	NPC44240
0.8667	High Similarity	NPC474728
0.8652	High Similarity	NPC472220
0.8652	High Similarity	NPC471722
0.8652	High Similarity	NPC97884
0.8652	High Similarity	NPC183546
0.8652	High Similarity	NPC294480
0.8636	High Similarity	NPC72133
0.8621	High Similarity	NPC100391
0.8621	High Similarity	NPC165064
0.8617	High Similarity	NPC186810
0.8617	High Similarity	NPC48647
0.8605	High Similarity	NPC296367
0.8605	High Similarity	NPC260956
0.8602	High Similarity	NPC7124
0.8602	High Similarity	NPC96859
0.8602	High Similarity	NPC328162
0.8602	High Similarity	NPC305483
0.8602	High Similarity	NPC42042
0.8587	High Similarity	NPC471720
0.8587	High Similarity	NPC184006
0.8587	High Similarity	NPC49670
0.8587	High Similarity	NPC474922
0.8587	High Similarity	NPC296164
0.8587	High Similarity	NPC74751
0.8587	High Similarity	NPC23621
0.8587	High Similarity	NPC78580
0.8571	High Similarity	NPC154101
0.8571	High Similarity	NPC160506
0.8571	High Similarity	NPC471901
0.8556	High Similarity	NPC54689
0.8556	High Similarity	NPC275740
0.8556	High Similarity	NPC86319
0.8556	High Similarity	NPC128496
0.8542	High Similarity	NPC22388
0.8539	High Similarity	NPC33768
0.8539	High Similarity	NPC162107
0.8539	High Similarity	NPC46912
0.8539	High Similarity	NPC96496
0.8539	High Similarity	NPC312215
0.8523	High Similarity	NPC98270
0.8511	High Similarity	NPC108078
0.8511	High Similarity	NPC320306
0.8511	High Similarity	NPC141401
0.8506	High Similarity	NPC69279
0.8506	High Similarity	NPC83569
0.8495	Intermediate Similarity	NPC195715
0.8495	Intermediate Similarity	NPC23241
0.8495	Intermediate Similarity	NPC84383
0.8495	Intermediate Similarity	NPC474727
0.8488	Intermediate Similarity	NPC147066
0.8488	Intermediate Similarity	NPC473420
0.8478	Intermediate Similarity	NPC152897
0.8478	Intermediate Similarity	NPC474436
0.8478	Intermediate Similarity	NPC477855
0.8478	Intermediate Similarity	NPC287118
0.8478	Intermediate Similarity	NPC473690
0.8478	Intermediate Similarity	NPC63118
0.8478	Intermediate Similarity	NPC66429
0.8478	Intermediate Similarity	NPC49776
0.8478	Intermediate Similarity	NPC471902
0.8471	Intermediate Similarity	NPC477371
0.8469	Intermediate Similarity	NPC278628
0.8469	Intermediate Similarity	NPC475494
0.8469	Intermediate Similarity	NPC231530
0.8462	Intermediate Similarity	NPC123854
0.8462	Intermediate Similarity	NPC191684
0.8462	Intermediate Similarity	NPC477149
0.8462	Intermediate Similarity	NPC477147
0.8454	Intermediate Similarity	NPC180204
0.8444	Intermediate Similarity	NPC52169
0.8444	Intermediate Similarity	NPC471724
0.8444	Intermediate Similarity	NPC182797
0.8444	Intermediate Similarity	NPC143767
0.8444	Intermediate Similarity	NPC131470
0.8444	Intermediate Similarity	NPC24816
0.8444	Intermediate Similarity	NPC246708
0.8444	Intermediate Similarity	NPC40552
0.8438	Intermediate Similarity	NPC99411
0.8427	Intermediate Similarity	NPC91525
0.8427	Intermediate Similarity	NPC12774
0.8427	Intermediate Similarity	NPC9892
0.8427	Intermediate Similarity	NPC329943
0.8427	Intermediate Similarity	NPC6979
0.8427	Intermediate Similarity	NPC212843
0.8427	Intermediate Similarity	NPC2783
0.8427	Intermediate Similarity	NPC10005
0.8421	Intermediate Similarity	NPC477854
0.8409	Intermediate Similarity	NPC475509
0.8409	Intermediate Similarity	NPC59453
0.8409	Intermediate Similarity	NPC221758
0.8409	Intermediate Similarity	NPC473246
0.8404	Intermediate Similarity	NPC327179
0.8404	Intermediate Similarity	NPC456
0.8404	Intermediate Similarity	NPC230151
0.8404	Intermediate Similarity	NPC328371
0.8404	Intermediate Similarity	NPC472941
0.84	Intermediate Similarity	NPC265655
0.8391	Intermediate Similarity	NPC73882
0.8391	Intermediate Similarity	NPC133391
0.8391	Intermediate Similarity	NPC240302
0.8387	Intermediate Similarity	NPC184870
0.8384	Intermediate Similarity	NPC220974
0.837	Intermediate Similarity	NPC475416
0.837	Intermediate Similarity	NPC150383
0.8367	Intermediate Similarity	NPC472227
0.8367	Intermediate Similarity	NPC472228
0.8367	Intermediate Similarity	NPC471293
0.8353	Intermediate Similarity	NPC321514
0.8352	Intermediate Similarity	NPC198664
0.8352	Intermediate Similarity	NPC59263
0.8352	Intermediate Similarity	NPC475049
0.8352	Intermediate Similarity	NPC130520
0.8352	Intermediate Similarity	NPC476733
0.8352	Intermediate Similarity	NPC127689
0.8352	Intermediate Similarity	NPC474245
0.8352	Intermediate Similarity	NPC121798
0.8352	Intermediate Similarity	NPC263393
0.8352	Intermediate Similarity	NPC215029
0.8352	Intermediate Similarity	NPC61543
0.8352	Intermediate Similarity	NPC225585
0.8352	Intermediate Similarity	NPC32830
0.8352	Intermediate Similarity	NPC470588

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 NPC111585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1370
0.2-0.3	3935
0.3-0.4	2497
0.4-0.5	684
0.5-0.6	195
0.6-0.7	178
0.7-0.8	142
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD6399	Phase 3
0.8587	High Similarity	NPD7748	Approved
0.8571	High Similarity	NPD8034	Phase 2
0.8571	High Similarity	NPD8035	Phase 2
0.8409	Intermediate Similarity	NPD4786	Approved
0.8352	Intermediate Similarity	NPD5328	Approved
0.8316	Intermediate Similarity	NPD7902	Approved
0.8315	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD5695	Phase 3
0.8283	Intermediate Similarity	NPD7128	Approved
0.8283	Intermediate Similarity	NPD6402	Approved
0.8283	Intermediate Similarity	NPD6675	Approved
0.8283	Intermediate Similarity	NPD5739	Approved
0.8242	Intermediate Similarity	NPD6672	Approved
0.8242	Intermediate Similarity	NPD5737	Approved
0.8222	Intermediate Similarity	NPD3618	Phase 1
0.8222	Intermediate Similarity	NPD7146	Approved
0.8222	Intermediate Similarity	NPD5330	Approved
0.8222	Intermediate Similarity	NPD7334	Approved
0.8222	Intermediate Similarity	NPD6409	Approved
0.8222	Intermediate Similarity	NPD6684	Approved
0.8222	Intermediate Similarity	NPD7521	Approved
0.8182	Intermediate Similarity	NPD3667	Approved
0.8172	Intermediate Similarity	NPD7515	Phase 2
0.8172	Intermediate Similarity	NPD6079	Approved
0.8125	Intermediate Similarity	NPD6083	Phase 2
0.8125	Intermediate Similarity	NPD6084	Phase 2
0.8119	Intermediate Similarity	NPD6881	Approved
0.8119	Intermediate Similarity	NPD7320	Approved
0.8119	Intermediate Similarity	NPD6899	Approved
0.8058	Intermediate Similarity	NPD8130	Phase 1
0.8043	Intermediate Similarity	NPD6903	Approved
0.8043	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD7638	Approved
0.8039	Intermediate Similarity	NPD6372	Approved
0.8039	Intermediate Similarity	NPD6373	Approved
0.802	Intermediate Similarity	NPD5697	Approved
0.802	Intermediate Similarity	NPD5701	Approved
0.8	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7900	Approved
0.7981	Intermediate Similarity	NPD8297	Approved
0.7961	Intermediate Similarity	NPD7102	Approved
0.7961	Intermediate Similarity	NPD6883	Approved
0.7961	Intermediate Similarity	NPD7290	Approved
0.7959	Intermediate Similarity	NPD7640	Approved
0.7959	Intermediate Similarity	NPD7639	Approved
0.7941	Intermediate Similarity	NPD6011	Approved
0.7917	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4202	Approved
0.7885	Intermediate Similarity	NPD6649	Approved
0.7885	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6650	Approved
0.7885	Intermediate Similarity	NPD6869	Approved
0.7885	Intermediate Similarity	NPD6617	Approved
0.7885	Intermediate Similarity	NPD6847	Approved
0.7864	Intermediate Similarity	NPD6012	Approved
0.7864	Intermediate Similarity	NPD6014	Approved
0.7864	Intermediate Similarity	NPD6013	Approved
0.7857	Intermediate Similarity	NPD5696	Approved
0.7835	Intermediate Similarity	NPD5222	Approved
0.7835	Intermediate Similarity	NPD4697	Phase 3
0.7835	Intermediate Similarity	NPD5221	Approved
0.7835	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5279	Phase 3
0.7826	Intermediate Similarity	NPD6098	Approved
0.781	Intermediate Similarity	NPD6882	Approved
0.7802	Intermediate Similarity	NPD3133	Approved
0.7802	Intermediate Similarity	NPD3666	Approved
0.7802	Intermediate Similarity	NPD3668	Phase 3
0.7802	Intermediate Similarity	NPD3665	Phase 1
0.7789	Intermediate Similarity	NPD6411	Approved
0.7789	Intermediate Similarity	NPD5284	Approved
0.7789	Intermediate Similarity	NPD5281	Approved
0.7789	Intermediate Similarity	NPD6050	Approved
0.7766	Intermediate Similarity	NPD6673	Approved
0.7766	Intermediate Similarity	NPD6080	Approved
0.7766	Intermediate Similarity	NPD6904	Approved
0.7755	Intermediate Similarity	NPD5173	Approved
0.7755	Intermediate Similarity	NPD4755	Approved
0.7753	Intermediate Similarity	NPD7525	Registered
0.7701	Intermediate Similarity	NPD6117	Approved
0.7684	Intermediate Similarity	NPD5692	Phase 3
0.7614	Intermediate Similarity	NPD6116	Phase 1
0.7604	Intermediate Similarity	NPD5694	Approved
0.76	Intermediate Similarity	NPD5286	Approved
0.76	Intermediate Similarity	NPD4700	Approved
0.76	Intermediate Similarity	NPD4696	Approved
0.76	Intermediate Similarity	NPD5285	Approved
0.7593	Intermediate Similarity	NPD6868	Approved
0.7586	Intermediate Similarity	NPD6942	Approved
0.7586	Intermediate Similarity	NPD7339	Approved
0.7582	Intermediate Similarity	NPD4223	Phase 3
0.7582	Intermediate Similarity	NPD4221	Approved
0.7579	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4753	Phase 2
0.7579	Intermediate Similarity	NPD6101	Approved
0.7573	Intermediate Similarity	NPD6008	Approved
0.7528	Intermediate Similarity	NPD6697	Approved
0.7528	Intermediate Similarity	NPD6118	Approved
0.7528	Intermediate Similarity	NPD6115	Approved
0.7528	Intermediate Similarity	NPD6114	Approved
0.7527	Intermediate Similarity	NPD5329	Approved
0.7525	Intermediate Similarity	NPD5223	Approved
0.7523	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD5207	Approved
0.7474	Intermediate Similarity	NPD5208	Approved
0.7471	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6335	Approved
0.7451	Intermediate Similarity	NPD5224	Approved
0.7451	Intermediate Similarity	NPD5211	Phase 2
0.7451	Intermediate Similarity	NPD5225	Approved
0.7451	Intermediate Similarity	NPD5226	Approved
0.7451	Intermediate Similarity	NPD4633	Approved
0.7449	Intermediate Similarity	NPD6001	Approved
0.7447	Intermediate Similarity	NPD5280	Approved
0.7447	Intermediate Similarity	NPD4694	Approved
0.7447	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5690	Phase 2
0.7431	Intermediate Similarity	NPD6274	Approved
0.7423	Intermediate Similarity	NPD5693	Phase 1
0.7419	Intermediate Similarity	NPD4197	Approved
0.7407	Intermediate Similarity	NPD4632	Approved
0.7396	Intermediate Similarity	NPD6051	Approved
0.7387	Intermediate Similarity	NPD7101	Approved
0.7387	Intermediate Similarity	NPD7100	Approved
0.7379	Intermediate Similarity	NPD5175	Approved
0.7379	Intermediate Similarity	NPD5174	Approved
0.7379	Intermediate Similarity	NPD4754	Approved
0.7368	Intermediate Similarity	NPD3573	Approved
0.7364	Intermediate Similarity	NPD6317	Approved
0.7333	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5141	Approved
0.7303	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6313	Approved
0.7297	Intermediate Similarity	NPD6314	Approved
0.7283	Intermediate Similarity	NPD4692	Approved
0.7283	Intermediate Similarity	NPD4139	Approved
0.7282	Intermediate Similarity	NPD7632	Discontinued
0.7263	Intermediate Similarity	NPD4688	Approved
0.7263	Intermediate Similarity	NPD5205	Approved
0.7263	Intermediate Similarity	NPD4693	Phase 3
0.7263	Intermediate Similarity	NPD4689	Approved
0.7263	Intermediate Similarity	NPD4138	Approved
0.7263	Intermediate Similarity	NPD4690	Approved
0.7257	Intermediate Similarity	NPD6908	Approved
0.7257	Intermediate Similarity	NPD6909	Approved
0.7253	Intermediate Similarity	NPD7645	Phase 2
0.7238	Intermediate Similarity	NPD4767	Approved
0.7238	Intermediate Similarity	NPD4768	Approved
0.7216	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6009	Approved
0.7204	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4629	Approved
0.72	Intermediate Similarity	NPD5654	Approved
0.72	Intermediate Similarity	NPD5210	Approved
0.7196	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD5779	Approved
0.717	Intermediate Similarity	NPD6412	Phase 2
0.7168	Intermediate Similarity	NPD6319	Approved
0.7158	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.713	Intermediate Similarity	NPD7604	Phase 2
0.7128	Intermediate Similarity	NPD4788	Approved
0.7128	Intermediate Similarity	NPD5362	Discontinued
0.7105	Intermediate Similarity	NPD5983	Phase 2
0.7105	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4730	Approved
0.7103	Intermediate Similarity	NPD5128	Approved
0.7103	Intermediate Similarity	NPD5168	Approved
0.7103	Intermediate Similarity	NPD4729	Approved
0.7094	Intermediate Similarity	NPD8293	Discontinued
0.7087	Intermediate Similarity	NPD6404	Discontinued
0.7079	Intermediate Similarity	NPD5733	Approved
0.7071	Intermediate Similarity	NPD7637	Suspended
0.7069	Intermediate Similarity	NPD7492	Approved
0.7059	Intermediate Similarity	NPD5959	Approved
0.7045	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4243	Approved
0.7045	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7736	Approved
0.7021	Intermediate Similarity	NPD6435	Approved
0.7018	Intermediate Similarity	NPD6059	Approved
0.7018	Intermediate Similarity	NPD6054	Approved
0.7009	Intermediate Similarity	NPD6336	Discontinued
0.7009	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD3702	Approved
0.699	Remote Similarity	NPD4225	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.6989	Remote Similarity	NPD4748	Discontinued
0.6972	Remote Similarity	NPD5250	Approved
0.6972	Remote Similarity	NPD5249	Phase 3
0.6972	Remote Similarity	NPD5248	Approved
0.6972	Remote Similarity	NPD5247	Approved
0.6972	Remote Similarity	NPD5135	Approved
0.6972	Remote Similarity	NPD5169	Approved
0.6972	Remote Similarity	NPD5251	Approved
0.6972	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4634	Approved
0.697	Remote Similarity	NPD4096	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