NPASS Compound

Structure

CID129689 OpenBabel06191715482D 41 44 0 0 1 0 0 0 0 0999 V2000 -0.8495 9.2107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8244 2.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1979 4.1011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3878 -2.9681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2651 -2.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5405 0.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3608 8.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 7.5187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3594 3.2889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8481 4.1348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2334 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3869 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3604 6.6729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6943 -1.9552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 2.4428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5003 3.1712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8473 -1.4665 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5411 -1.4661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2336 -1.4656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6926 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3599 4.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 -0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6938 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6935 0.9777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 1.4664 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3875 -1.9547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5408 -0.4882 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9773 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 2.4569 2.9682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0205 -1.9679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1018 -1.9663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4010 -0.7094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6170 4.9812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5613 1.4791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8485 5.8267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 2.4443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 3 19 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 7 32 1 0 0 0 0 9 10 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 31 1 0 0 0 0 15 40 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 2 1 6 0 0 0 18 20 1 0 0 0 0 19 34 2 0 0 0 0 19 41 1 0 0 0 0 20 32 1 6 0 0 0 21 26 1 0 0 0 0 21 35 1 6 0 0 0 22 30 1 0 0 0 0 22 31 1 6 0 0 0 23 30 1 0 0 0 0 23 36 1 6 0 0 0 24 33 1 0 0 0 0 24 37 2 0 0 0 0 25 38 2 0 0 0 0 25 40 1 0 0 0 0 26 27 2 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 28 29 1 0 0 0 0 28 39 2 0 0 0 0 29 32 1 6 0 0 0 29 41 1 0 0 0 0 31 6 1 6 0 0 0 32 33 1 6 0 0 0 33 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.35
Volume:	602.238
LogP:	4.149
LogD:	2.995
LogS:	-4.23
# Rotatable Bonds:	10
TPSA:	124.04
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	5.131
Fsp3:	0.848
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.127
MDCK Permeability:	3.353390275151469e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.169
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.83
Plasma Protein Binding (PPB):	72.28388214111328%
Volume Distribution (VD):	0.476
Pgp-substrate:	21.91696548461914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.324
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.691

ADMET: Excretion

Clearance (CL):	9.3
Half-life (T1/2):	0.454

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.373
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.124
Carcinogencity:	0.029
Eye Corrosion:	0.472
Eye Irritation:	0.104
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC129689

Natural Product ID:	NPC129689
*Common Name:**	Butyl Lucidenate P
IUPAC Name:	butyl (4R)-4-[(3S,5R,7S,10S,12S,13R,14R,17R)-12-acetyloxy-3,7-dihydroxy-4,4,10,13,14-pentamethyl-11,15-dioxo-2,3,5,6,7,12,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Synonyms:	Butyl Lucidenate P
Standard InCHIKey:	KLJAWVAKODZGOX-WPVPHOMXSA-N
Standard InCHI:	InChI=1S/C33H50O8/c1-9-10-15-40-25(38)12-11-18(2)20-16-24(37)33(8)26-21(35)17-22-30(4,5)23(36)13-14-31(22,6)27(26)28(39)29(32(20,33)7)41-19(3)34/h18,20-23,29,35-36H,9-17H2,1-8H3/t18-,20-,21+,22+,23+,29-,31+,32+,33+/m1/s1
SMILES:	CCCCOC(=O)CC[C@H]([C@H]1CC(=O)[C@@]2([C@]1(C)[C@H](OC(=O)C)C(=O)C1=C2[C@@H](O)C[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337648
PubChem CID:	71561376
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]
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]
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]
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]
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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	7400.0	nM	PMID[545345]

☑ 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 NPC129689 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	234
0.1-0.2	1533
0.2-0.3	5002
0.3-0.4	8917
0.4-0.5	12341
0.5-0.6	7166
0.6-0.7	5744
0.7-0.8	1590
0.8-0.85	107
0.85-0.9	46
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC115303
0.9901	High Similarity	NPC286174
0.9901	High Similarity	NPC77947
0.9439	High Similarity	NPC472927
0.9412	High Similarity	NPC51452
0.9406	High Similarity	NPC251017
0.9314	High Similarity	NPC135854
0.9314	High Similarity	NPC2436
0.9314	High Similarity	NPC216245
0.9314	High Similarity	NPC470251
0.9266	High Similarity	NPC472933
0.9238	High Similarity	NPC272898
0.9238	High Similarity	NPC473036
0.9216	High Similarity	NPC33973
0.9216	High Similarity	NPC70967
0.9159	High Similarity	NPC472926
0.9118	High Similarity	NPC281702
0.9118	High Similarity	NPC53222
0.9109	High Similarity	NPC307954
0.902	High Similarity	NPC124211
0.8981	High Similarity	NPC472929
0.8972	High Similarity	NPC472928
0.8952	High Similarity	NPC473037
0.8922	High Similarity	NPC144660
0.8922	High Similarity	NPC157787
0.8922	High Similarity	NPC299971
0.8922	High Similarity	NPC88198
0.8911	High Similarity	NPC121339
0.8911	High Similarity	NPC122294
0.8909	High Similarity	NPC472934
0.8868	High Similarity	NPC295244
0.8824	High Similarity	NPC16021
0.8824	High Similarity	NPC275439
0.8824	High Similarity	NPC112753
0.8812	High Similarity	NPC3772
0.8812	High Similarity	NPC7124
0.8762	High Similarity	NPC28656
0.8738	High Similarity	NPC327431
0.8725	High Similarity	NPC106557
0.8725	High Similarity	NPC216904
0.8713	High Similarity	NPC37646
0.8667	High Similarity	NPC55872
0.8627	High Similarity	NPC243525
0.8627	High Similarity	NPC40765
0.8614	High Similarity	NPC184870
0.8598	High Similarity	NPC472925
0.8571	High Similarity	NPC308726
0.8571	High Similarity	NPC56498
0.8571	High Similarity	NPC119601
0.8571	High Similarity	NPC293753
0.8571	High Similarity	NPC234892
0.8545	High Similarity	NPC264634
0.8545	High Similarity	NPC147180
0.8544	High Similarity	NPC43747
0.8544	High Similarity	NPC320306
0.8529	High Similarity	NPC297199
0.8529	High Similarity	NPC255809
0.8509	High Similarity	NPC109973
0.8482	Intermediate Similarity	NPC270958
0.8476	Intermediate Similarity	NPC163372
0.8476	Intermediate Similarity	NPC302537
0.8468	Intermediate Similarity	NPC202889
0.8447	Intermediate Similarity	NPC328162
0.8447	Intermediate Similarity	NPC328371
0.8447	Intermediate Similarity	NPC96859
0.8447	Intermediate Similarity	NPC305483
0.8381	Intermediate Similarity	NPC51370
0.8381	Intermediate Similarity	NPC287833
0.8381	Intermediate Similarity	NPC205899
0.8365	Intermediate Similarity	NPC18319
0.835	Intermediate Similarity	NPC317586
0.835	Intermediate Similarity	NPC469995
0.835	Intermediate Similarity	NPC318282
0.835	Intermediate Similarity	NPC173875
0.835	Intermediate Similarity	NPC470016
0.835	Intermediate Similarity	NPC174948
0.8333	Intermediate Similarity	NPC323834
0.8333	Intermediate Similarity	NPC118638
0.8333	Intermediate Similarity	NPC181357
0.8333	Intermediate Similarity	NPC470254
0.8319	Intermediate Similarity	NPC148458
0.8318	Intermediate Similarity	NPC275583
0.8304	Intermediate Similarity	NPC962
0.8286	Intermediate Similarity	NPC10364
0.8273	Intermediate Similarity	NPC304495
0.8269	Intermediate Similarity	NPC125622
0.8269	Intermediate Similarity	NPC95565
0.8252	Intermediate Similarity	NPC166906
0.8246	Intermediate Similarity	NPC471854
0.8241	Intermediate Similarity	NPC96268
0.8235	Intermediate Similarity	NPC107690
0.8224	Intermediate Similarity	NPC136289
0.8224	Intermediate Similarity	NPC475558
0.8224	Intermediate Similarity	NPC473788
0.8214	Intermediate Similarity	NPC280782
0.8214	Intermediate Similarity	NPC170487
0.8214	Intermediate Similarity	NPC71348
0.8208	Intermediate Similarity	NPC472972
0.8208	Intermediate Similarity	NPC476274
0.8205	Intermediate Similarity	NPC222688
0.8198	Intermediate Similarity	NPC197428
0.819	Intermediate Similarity	NPC17938
0.8182	Intermediate Similarity	NPC94529
0.8173	Intermediate Similarity	NPC477437
0.8173	Intermediate Similarity	NPC477438
0.8173	Intermediate Similarity	NPC241156
0.8165	Intermediate Similarity	NPC196528
0.8158	Intermediate Similarity	NPC266728
0.8158	Intermediate Similarity	NPC49492
0.8148	Intermediate Similarity	NPC159442
0.8148	Intermediate Similarity	NPC236390
0.8142	Intermediate Similarity	NPC250109
0.8131	Intermediate Similarity	NPC476223
0.8131	Intermediate Similarity	NPC476240
0.8131	Intermediate Similarity	NPC81530
0.8131	Intermediate Similarity	NPC472924
0.8131	Intermediate Similarity	NPC224720
0.8125	Intermediate Similarity	NPC34315
0.8125	Intermediate Similarity	NPC214797
0.8125	Intermediate Similarity	NPC231589
0.8125	Intermediate Similarity	NPC118860
0.812	Intermediate Similarity	NPC202051
0.8095	Intermediate Similarity	NPC42042
0.8095	Intermediate Similarity	NPC472941
0.8095	Intermediate Similarity	NPC456
0.8091	Intermediate Similarity	NPC475294
0.8087	Intermediate Similarity	NPC239273
0.8077	Intermediate Similarity	NPC477439
0.8077	Intermediate Similarity	NPC474922
0.8058	Intermediate Similarity	NPC63748
0.8058	Intermediate Similarity	NPC233116
0.8056	Intermediate Similarity	NPC195290
0.8056	Intermediate Similarity	NPC80781
0.8056	Intermediate Similarity	NPC204450
0.8053	Intermediate Similarity	NPC475524
0.8053	Intermediate Similarity	NPC285956
0.8053	Intermediate Similarity	NPC100267
0.8053	Intermediate Similarity	NPC221144
0.8037	Intermediate Similarity	NPC198880
0.8037	Intermediate Similarity	NPC316964
0.8037	Intermediate Similarity	NPC241221
0.8036	Intermediate Similarity	NPC286880
0.8036	Intermediate Similarity	NPC470496
0.8019	Intermediate Similarity	NPC23680
0.8018	Intermediate Similarity	NPC476479
0.8017	Intermediate Similarity	NPC257457
0.8017	Intermediate Similarity	NPC311554
0.8017	Intermediate Similarity	NPC21326
0.8	Intermediate Similarity	NPC50535
0.8	Intermediate Similarity	NPC63186
0.8	Intermediate Similarity	NPC231530
0.8	Intermediate Similarity	NPC278628
0.8	Intermediate Similarity	NPC475571
0.8	Intermediate Similarity	NPC472935
0.8	Intermediate Similarity	NPC48330
0.8	Intermediate Similarity	NPC200702
0.7982	Intermediate Similarity	NPC249187
0.7982	Intermediate Similarity	NPC52634
0.7982	Intermediate Similarity	NPC55954
0.7982	Intermediate Similarity	NPC85742
0.7982	Intermediate Similarity	NPC218513
0.7982	Intermediate Similarity	NPC25909
0.7982	Intermediate Similarity	NPC247957
0.7981	Intermediate Similarity	NPC477436
0.7981	Intermediate Similarity	NPC25750
0.7981	Intermediate Similarity	NPC69454
0.7981	Intermediate Similarity	NPC477435
0.7965	Intermediate Similarity	NPC43775
0.7965	Intermediate Similarity	NPC470281
0.7965	Intermediate Similarity	NPC188738
0.7961	Intermediate Similarity	NPC477147
0.7961	Intermediate Similarity	NPC477149
0.7961	Intermediate Similarity	NPC20388
0.7949	Intermediate Similarity	NPC268958
0.7949	Intermediate Similarity	NPC475041
0.7946	Intermediate Similarity	NPC470615
0.7946	Intermediate Similarity	NPC241927
0.7946	Intermediate Similarity	NPC258543
0.7946	Intermediate Similarity	NPC141350
0.7944	Intermediate Similarity	NPC114274
0.7944	Intermediate Similarity	NPC197386
0.7944	Intermediate Similarity	NPC471717
0.7944	Intermediate Similarity	NPC478056
0.7931	Intermediate Similarity	NPC55296
0.7928	Intermediate Similarity	NPC185
0.7928	Intermediate Similarity	NPC144854
0.7928	Intermediate Similarity	NPC3316
0.7925	Intermediate Similarity	NPC173272
0.7925	Intermediate Similarity	NPC249954
0.7913	Intermediate Similarity	NPC474181
0.7913	Intermediate Similarity	NPC473798
0.7909	Intermediate Similarity	NPC29705
0.7909	Intermediate Similarity	NPC47281
0.7909	Intermediate Similarity	NPC72255
0.7905	Intermediate Similarity	NPC245972
0.7905	Intermediate Similarity	NPC471720
0.7905	Intermediate Similarity	NPC196485
0.7903	Intermediate Similarity	NPC469674
0.7899	Intermediate Similarity	NPC269642
0.789	Intermediate Similarity	NPC471119

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 NPC129689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1971
0.2-0.3	3834
0.3-0.4	2032
0.4-0.5	647
0.5-0.6	212
0.6-0.7	171
0.7-0.8	75
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
0.8108	Intermediate Similarity	NPD6372	Approved
0.8108	Intermediate Similarity	NPD6373	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7965	Intermediate Similarity	NPD6649	Approved
0.7965	Intermediate Similarity	NPD6650	Approved
0.7895	Intermediate Similarity	NPD8297	Approved
0.7857	Intermediate Similarity	NPD6881	Approved
0.7857	Intermediate Similarity	NPD7320	Approved
0.7857	Intermediate Similarity	NPD6899	Approved
0.7807	Intermediate Similarity	NPD8130	Phase 1
0.7768	Intermediate Similarity	NPD5701	Approved
0.7768	Intermediate Similarity	NPD5697	Approved
0.7739	Intermediate Similarity	NPD6882	Approved
0.7719	Intermediate Similarity	NPD6883	Approved
0.7719	Intermediate Similarity	NPD7102	Approved
0.7719	Intermediate Similarity	NPD7290	Approved
0.7706	Intermediate Similarity	NPD7640	Approved
0.7706	Intermediate Similarity	NPD7639	Approved
0.7699	Intermediate Similarity	NPD6011	Approved
0.7652	Intermediate Similarity	NPD6869	Approved
0.7652	Intermediate Similarity	NPD6847	Approved
0.7652	Intermediate Similarity	NPD6617	Approved
0.7652	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6012	Approved
0.7632	Intermediate Similarity	NPD6014	Approved
0.7632	Intermediate Similarity	NPD6013	Approved
0.7615	Intermediate Similarity	NPD5696	Approved
0.7615	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD4697	Phase 3
0.7583	Intermediate Similarity	NPD6319	Approved
0.7568	Intermediate Similarity	NPD7632	Discontinued
0.7524	Intermediate Similarity	NPD5328	Approved
0.7523	Intermediate Similarity	NPD6083	Phase 2
0.7523	Intermediate Similarity	NPD6084	Phase 2
0.7522	Intermediate Similarity	NPD6008	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD5695	Phase 3
0.7479	Intermediate Similarity	NPD6009	Approved
0.7477	Intermediate Similarity	NPD6399	Phase 3
0.7431	Intermediate Similarity	NPD5221	Approved
0.7431	Intermediate Similarity	NPD5222	Approved
0.7431	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5737	Approved
0.7429	Intermediate Similarity	NPD6672	Approved
0.7411	Intermediate Similarity	NPD5211	Phase 2
0.7398	Intermediate Similarity	NPD7604	Phase 2
0.7395	Intermediate Similarity	NPD6868	Approved
0.7383	Intermediate Similarity	NPD6079	Approved
0.7377	Intermediate Similarity	NPD5983	Phase 2
0.7364	Intermediate Similarity	NPD5173	Approved
0.7364	Intermediate Similarity	NPD4755	Approved
0.736	Intermediate Similarity	NPD8293	Discontinued
0.7339	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7115	Discovery
0.7302	Intermediate Similarity	NPD7736	Approved
0.7295	Intermediate Similarity	NPD6054	Approved
0.7295	Intermediate Similarity	NPD6059	Approved
0.7281	Intermediate Similarity	NPD5141	Approved
0.728	Intermediate Similarity	NPD6616	Approved
0.728	Intermediate Similarity	NPD6336	Discontinued
0.7273	Intermediate Similarity	NPD6335	Approved
0.7266	Intermediate Similarity	NPD7260	Phase 2
0.7258	Intermediate Similarity	NPD8328	Phase 3
0.725	Intermediate Similarity	NPD6274	Approved
0.7248	Intermediate Similarity	NPD7748	Approved
0.7238	Intermediate Similarity	NPD3618	Phase 1
0.7232	Intermediate Similarity	NPD4696	Approved
0.7232	Intermediate Similarity	NPD5286	Approved
0.7232	Intermediate Similarity	NPD5285	Approved
0.7232	Intermediate Similarity	NPD4700	Approved
0.7222	Intermediate Similarity	NPD7078	Approved
0.7213	Intermediate Similarity	NPD7100	Approved
0.7213	Intermediate Similarity	NPD7101	Approved
0.7209	Intermediate Similarity	NPD6845	Suspended
0.7207	Intermediate Similarity	NPD7902	Approved
0.719	Intermediate Similarity	NPD6317	Approved
0.7179	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6370	Approved
0.7168	Intermediate Similarity	NPD5223	Approved
0.7131	Intermediate Similarity	NPD6314	Approved
0.7131	Intermediate Similarity	NPD6313	Approved
0.7119	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5224	Approved
0.7105	Intermediate Similarity	NPD5225	Approved
0.7105	Intermediate Similarity	NPD5226	Approved
0.7105	Intermediate Similarity	NPD4633	Approved
0.7097	Intermediate Similarity	NPD6016	Approved
0.7097	Intermediate Similarity	NPD6909	Approved
0.7097	Intermediate Similarity	NPD6015	Approved
0.7097	Intermediate Similarity	NPD6908	Approved
0.7075	Intermediate Similarity	NPD5279	Phase 3
0.7069	Intermediate Similarity	NPD4767	Approved
0.7069	Intermediate Similarity	NPD4768	Approved
0.7064	Intermediate Similarity	NPD7515	Phase 2
0.7064	Intermediate Similarity	NPD6050	Approved
0.7064	Intermediate Similarity	NPD8034	Phase 2
0.7064	Intermediate Similarity	NPD8035	Phase 2
0.7048	Intermediate Similarity	NPD4786	Approved
0.7043	Intermediate Similarity	NPD5175	Approved
0.7043	Intermediate Similarity	NPD5174	Approved
0.7043	Intermediate Similarity	NPD4754	Approved
0.704	Intermediate Similarity	NPD5988	Approved
0.7037	Intermediate Similarity	NPD6904	Approved
0.7037	Intermediate Similarity	NPD6673	Approved
0.7037	Intermediate Similarity	NPD6080	Approved
0.7034	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5210	Approved
0.7027	Intermediate Similarity	NPD4629	Approved
0.7008	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.7	Intermediate Similarity	NPD6053	Discontinued
0.6975	Remote Similarity	NPD4634	Approved
0.6972	Remote Similarity	NPD5692	Phase 3
0.696	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4730	Approved
0.6949	Remote Similarity	NPD4729	Approved
0.6937	Remote Similarity	NPD7900	Approved
0.6937	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7334	Approved
0.6916	Remote Similarity	NPD6409	Approved
0.6916	Remote Similarity	NPD6684	Approved
0.6916	Remote Similarity	NPD7146	Approved
0.6916	Remote Similarity	NPD7521	Approved
0.6916	Remote Similarity	NPD5330	Approved
0.6909	Remote Similarity	NPD5693	Phase 1
0.6909	Remote Similarity	NPD5694	Approved
0.6899	Remote Similarity	NPD6033	Approved
0.6881	Remote Similarity	NPD4753	Phase 2
0.6875	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3667	Approved
0.6847	Remote Similarity	NPD4202	Approved
0.6846	Remote Similarity	NPD7319	Approved
0.6833	Remote Similarity	NPD5250	Approved
0.6833	Remote Similarity	NPD5249	Phase 3
0.6833	Remote Similarity	NPD5251	Approved
0.6833	Remote Similarity	NPD5247	Approved
0.6833	Remote Similarity	NPD5248	Approved
0.6822	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5128	Approved
0.6807	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5168	Approved
0.6796	Remote Similarity	NPD3617	Approved
0.6796	Remote Similarity	NPD6114	Approved
0.6796	Remote Similarity	NPD6115	Approved
0.6796	Remote Similarity	NPD6118	Approved
0.6796	Remote Similarity	NPD6697	Approved
0.6789	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6903	Approved
0.6759	Remote Similarity	NPD6098	Approved
0.6757	Remote Similarity	NPD5281	Approved
0.6757	Remote Similarity	NPD6411	Approved
0.6757	Remote Similarity	NPD5284	Approved
0.6729	Remote Similarity	NPD3665	Phase 1
0.6729	Remote Similarity	NPD3133	Approved
0.6729	Remote Similarity	NPD3666	Approved
0.6727	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5654	Approved
0.6723	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5135	Approved
0.6694	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6639	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD5217	Approved
0.6639	Remote Similarity	NPD5215	Approved
0.6639	Remote Similarity	NPD5127	Approved
0.6609	Remote Similarity	NPD5959	Approved
0.6607	Remote Similarity	NPD7637	Suspended
0.6606	Remote Similarity	NPD4694	Approved
0.6606	Remote Similarity	NPD5690	Phase 2
0.6606	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5280	Approved
0.6602	Remote Similarity	NPD6117	Approved
0.6583	Remote Similarity	NPD6614	Approved
0.6577	Remote Similarity	NPD6101	Approved
0.6577	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4197	Approved
0.6569	Remote Similarity	NPD6334	Approved
0.6569	Remote Similarity	NPD6333	Approved
0.6562	Remote Similarity	NPD8033	Approved
0.6545	Remote Similarity	NPD3573	Approved
0.6538	Remote Similarity	NPD6116	Phase 1
0.6518	Remote Similarity	NPD5207	Approved
0.6518	Remote Similarity	NPD5785	Approved
0.6505	Remote Similarity	NPD3703	Phase 2
0.6491	Remote Similarity	NPD6001	Approved
0.6484	Remote Similarity	NPD8377	Approved
0.6484	Remote Similarity	NPD8294	Approved
0.648	Remote Similarity	NPD5167	Approved
0.6476	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7327	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