NPASS Compound

Structure

CID77947 OpenBabel06191715412D 38 41 0 0 1 0 0 0 0 0999 V2000 1.8209 -2.4378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1956 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3813 2.9624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2569 2.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5356 -0.5242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3597 -6.6601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3587 -3.2826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8464 -4.1269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2253 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3804 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6896 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6911 1.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 -2.4381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4974 -3.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 -1.4631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8457 1.4637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2255 1.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3592 -4.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -1.4636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3810 1.9510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5359 0.4873 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9754 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 -2.4522 -2.9625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0225 1.9653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0940 1.9637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3981 0.7096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6158 -4.9716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5584 -1.4774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8469 -5.8156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 -2.4396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 16 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 37 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 28 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 1 1 6 0 0 0 15 17 1 0 0 0 0 16 31 2 0 0 0 0 16 38 1 0 0 0 0 17 29 1 6 0 0 0 18 23 1 0 0 0 0 18 32 1 6 0 0 0 19 27 1 0 0 0 0 19 28 1 6 0 0 0 20 27 1 0 0 0 0 20 33 1 6 0 0 0 21 30 1 0 0 0 0 21 34 2 0 0 0 0 22 35 2 0 0 0 0 22 37 1 0 0 0 0 23 24 2 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 36 2 0 0 0 0 26 29 1 6 0 0 0 26 38 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.3
Volume:	550.35
LogP:	3.189
LogD:	2.082
LogS:	-3.81
# Rotatable Bonds:	7
TPSA:	124.04
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.532
Synthetic Accessibility Score:	5.128
Fsp3:	0.833
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:	-5.182
MDCK Permeability:	4.783152326126583e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.899

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	53.43012237548828%
Volume Distribution (VD):	0.379
Pgp-substrate:	37.86654281616211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.702

ADMET: Excretion

Clearance (CL):	7.639
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.66
Drug-inuced Liver Injury (DILI):	0.36
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.082
Carcinogencity:	0.03
Eye Corrosion:	0.433
Eye Irritation:	0.042
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC77947

Natural Product ID:	NPC77947
*Common Name:**	Methyl Lucidenate P
IUPAC Name:	methyl (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:	Methyl Lucidenate P
Standard InCHIKey:	PDTQBYSKJSRZCH-YQUZSDLJSA-N
Standard InCHI:	InChI=1S/C30H44O8/c1-15(9-10-22(35)37-8)17-13-21(34)30(7)23-18(32)14-19-27(3,4)20(33)11-12-28(19,5)24(23)25(36)26(29(17,30)6)38-16(2)31/h15,17-20,26,32-33H,9-14H2,1-8H3/t15-,17-,18+,19+,20+,26-,28+,29+,30+/m1/s1
SMILES:	COC(=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:	CHEMBL511952
PubChem CID:	11203394
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]
NPO25269	Ganoderma lucidum	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
Others	6

Activity Type	# Activity
Cell Line	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[506168]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	22.0	%	PMID[506169]
NPT2	Others	Unspecified		Activity	=	2.3	%	PMID[506168]
NPT2	Others	Unspecified		Activity	=	28.9	%	PMID[506168]
NPT2	Others	Unspecified		Activity	=	77.4	%	PMID[506168]
NPT2	Others	Unspecified		Activity	=	97.6	%	PMID[506168]
NPT2	Others	Unspecified		IC50	=	293.0	molar ratio	PMID[506168]

☑ 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 NPC77947 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	230
0.1-0.2	1505
0.2-0.3	4917
0.3-0.4	8810
0.4-0.5	12433
0.5-0.6	7302
0.6-0.7	5664
0.7-0.8	1649
0.8-0.85	122
0.85-0.9	45
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC286174
0.9901	High Similarity	NPC129689
0.9804	High Similarity	NPC115303
0.9505	High Similarity	NPC51452
0.95	High Similarity	NPC251017
0.9346	High Similarity	NPC472927
0.9327	High Similarity	NPC272898
0.9327	High Similarity	NPC473036
0.9307	High Similarity	NPC33973
0.9307	High Similarity	NPC70967
0.9216	High Similarity	NPC216245
0.9216	High Similarity	NPC2436
0.9216	High Similarity	NPC470251
0.9216	High Similarity	NPC135854
0.92	High Similarity	NPC307954
0.9174	High Similarity	NPC472933
0.9109	High Similarity	NPC124211
0.9065	High Similarity	NPC472926
0.9057	High Similarity	NPC472928
0.9038	High Similarity	NPC473037
0.902	High Similarity	NPC53222
0.902	High Similarity	NPC281702
0.901	High Similarity	NPC299971
0.901	High Similarity	NPC157787
0.901	High Similarity	NPC144660
0.901	High Similarity	NPC88198
0.9	High Similarity	NPC121339
0.9	High Similarity	NPC122294
0.8952	High Similarity	NPC295244
0.8911	High Similarity	NPC16021
0.89	High Similarity	NPC3772
0.89	High Similarity	NPC7124
0.8889	High Similarity	NPC472929
0.8846	High Similarity	NPC28656
0.8824	High Similarity	NPC327431
0.8818	High Similarity	NPC472934
0.8812	High Similarity	NPC216904
0.8812	High Similarity	NPC106557
0.88	High Similarity	NPC37646
0.875	High Similarity	NPC55872
0.8725	High Similarity	NPC112753
0.8725	High Similarity	NPC275439
0.8713	High Similarity	NPC243525
0.8713	High Similarity	NPC40765
0.87	High Similarity	NPC184870
0.8679	High Similarity	NPC472925
0.8654	High Similarity	NPC293753
0.8654	High Similarity	NPC308726
0.8654	High Similarity	NPC119601
0.8654	High Similarity	NPC234892
0.8627	High Similarity	NPC43747
0.8627	High Similarity	NPC320306
0.8614	High Similarity	NPC255809
0.8614	High Similarity	NPC297199
0.8584	High Similarity	NPC109973
0.8558	High Similarity	NPC163372
0.8558	High Similarity	NPC302537
0.8529	High Similarity	NPC328371
0.8529	High Similarity	NPC305483
0.8529	High Similarity	NPC328162
0.8529	High Similarity	NPC96859
0.8476	Intermediate Similarity	NPC56498
0.8462	Intermediate Similarity	NPC287833
0.8462	Intermediate Similarity	NPC51370
0.8462	Intermediate Similarity	NPC205899
0.8455	Intermediate Similarity	NPC147180
0.8455	Intermediate Similarity	NPC264634
0.8447	Intermediate Similarity	NPC18319
0.8431	Intermediate Similarity	NPC317586
0.8431	Intermediate Similarity	NPC318282
0.8431	Intermediate Similarity	NPC173875
0.8431	Intermediate Similarity	NPC469995
0.8431	Intermediate Similarity	NPC174948
0.8431	Intermediate Similarity	NPC470016
0.8416	Intermediate Similarity	NPC470254
0.8411	Intermediate Similarity	NPC323834
0.8411	Intermediate Similarity	NPC181357
0.8396	Intermediate Similarity	NPC275583
0.8393	Intermediate Similarity	NPC270958
0.8378	Intermediate Similarity	NPC202889
0.8378	Intermediate Similarity	NPC962
0.8365	Intermediate Similarity	NPC10364
0.835	Intermediate Similarity	NPC125622
0.835	Intermediate Similarity	NPC95565
0.8333	Intermediate Similarity	NPC166906
0.8318	Intermediate Similarity	NPC96268
0.8317	Intermediate Similarity	NPC107690
0.8302	Intermediate Similarity	NPC136289
0.8286	Intermediate Similarity	NPC472972
0.8286	Intermediate Similarity	NPC476274
0.8276	Intermediate Similarity	NPC222688
0.8252	Intermediate Similarity	NPC241156
0.8252	Intermediate Similarity	NPC477438
0.8252	Intermediate Similarity	NPC477437
0.8246	Intermediate Similarity	NPC118638
0.823	Intermediate Similarity	NPC148458
0.823	Intermediate Similarity	NPC49492
0.823	Intermediate Similarity	NPC266728
0.8224	Intermediate Similarity	NPC159442
0.8224	Intermediate Similarity	NPC236390
0.8214	Intermediate Similarity	NPC250109
0.8208	Intermediate Similarity	NPC81530
0.8208	Intermediate Similarity	NPC224720
0.8208	Intermediate Similarity	NPC476223
0.8208	Intermediate Similarity	NPC472924
0.8208	Intermediate Similarity	NPC476240
0.8198	Intermediate Similarity	NPC34315
0.8182	Intermediate Similarity	NPC304495
0.8173	Intermediate Similarity	NPC472941
0.8173	Intermediate Similarity	NPC456
0.8158	Intermediate Similarity	NPC471854
0.8155	Intermediate Similarity	NPC477439
0.8137	Intermediate Similarity	NPC63748
0.8137	Intermediate Similarity	NPC233116
0.8131	Intermediate Similarity	NPC473788
0.8131	Intermediate Similarity	NPC204450
0.8131	Intermediate Similarity	NPC195290
0.8131	Intermediate Similarity	NPC80781
0.8131	Intermediate Similarity	NPC475558
0.8125	Intermediate Similarity	NPC71348
0.8125	Intermediate Similarity	NPC170487
0.8125	Intermediate Similarity	NPC285956
0.8125	Intermediate Similarity	NPC280782
0.8113	Intermediate Similarity	NPC198880
0.8113	Intermediate Similarity	NPC316964
0.8108	Intermediate Similarity	NPC470496
0.8108	Intermediate Similarity	NPC197428
0.8108	Intermediate Similarity	NPC286880
0.8103	Intermediate Similarity	NPC17938
0.8095	Intermediate Similarity	NPC23680
0.8091	Intermediate Similarity	NPC94529
0.8091	Intermediate Similarity	NPC476479
0.8087	Intermediate Similarity	NPC21326
0.8077	Intermediate Similarity	NPC48330
0.8077	Intermediate Similarity	NPC200702
0.8073	Intermediate Similarity	NPC196528
0.8073	Intermediate Similarity	NPC50535
0.8067	Intermediate Similarity	NPC63186
0.8058	Intermediate Similarity	NPC25750
0.8058	Intermediate Similarity	NPC477435
0.8058	Intermediate Similarity	NPC69454
0.8058	Intermediate Similarity	NPC477436
0.8056	Intermediate Similarity	NPC247957
0.8056	Intermediate Similarity	NPC249187
0.8053	Intermediate Similarity	NPC25909
0.8039	Intermediate Similarity	NPC20388
0.8039	Intermediate Similarity	NPC477149
0.8039	Intermediate Similarity	NPC477147
0.8036	Intermediate Similarity	NPC214797
0.8036	Intermediate Similarity	NPC118860
0.8036	Intermediate Similarity	NPC188738
0.8036	Intermediate Similarity	NPC231589
0.8034	Intermediate Similarity	NPC202051
0.8019	Intermediate Similarity	NPC197386
0.8019	Intermediate Similarity	NPC478056
0.8019	Intermediate Similarity	NPC471717
0.8019	Intermediate Similarity	NPC114274
0.8018	Intermediate Similarity	NPC141350
0.8018	Intermediate Similarity	NPC470615
0.8017	Intermediate Similarity	NPC475041
0.8017	Intermediate Similarity	NPC268958
0.8	Intermediate Similarity	NPC144854
0.8	Intermediate Similarity	NPC239273
0.8	Intermediate Similarity	NPC173272
0.8	Intermediate Similarity	NPC42042
0.8	Intermediate Similarity	NPC185
0.8	Intermediate Similarity	NPC475294
0.8	Intermediate Similarity	NPC55296
0.8	Intermediate Similarity	NPC3316
0.8	Intermediate Similarity	NPC249954
0.7982	Intermediate Similarity	NPC72255
0.7982	Intermediate Similarity	NPC29705
0.7982	Intermediate Similarity	NPC47281
0.7982	Intermediate Similarity	NPC473798
0.7982	Intermediate Similarity	NPC474181
0.7981	Intermediate Similarity	NPC474922
0.7981	Intermediate Similarity	NPC245972
0.7981	Intermediate Similarity	NPC471720
0.7981	Intermediate Similarity	NPC196485
0.7966	Intermediate Similarity	NPC269642
0.7965	Intermediate Similarity	NPC221144
0.7965	Intermediate Similarity	NPC100267
0.7965	Intermediate Similarity	NPC475524
0.7963	Intermediate Similarity	NPC165250
0.7963	Intermediate Similarity	NPC295791
0.7946	Intermediate Similarity	NPC76084
0.7946	Intermediate Similarity	NPC210005
0.7944	Intermediate Similarity	NPC218383
0.7944	Intermediate Similarity	NPC471041
0.7944	Intermediate Similarity	NPC241221
0.7941	Intermediate Similarity	NPC214387
0.7931	Intermediate Similarity	NPC257457
0.7931	Intermediate Similarity	NPC311554
0.7928	Intermediate Similarity	NPC192813
0.7928	Intermediate Similarity	NPC275539
0.7928	Intermediate Similarity	NPC189075
0.7928	Intermediate Similarity	NPC65941
0.7928	Intermediate Similarity	NPC154608
0.7928	Intermediate Similarity	NPC277017
0.7925	Intermediate Similarity	NPC108078

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 NPC77947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1939
0.2-0.3	3803
0.3-0.4	2081
0.4-0.5	664
0.5-0.6	214
0.6-0.7	160
0.7-0.8	84
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
0.8182	Intermediate Similarity	NPD6373	Approved
0.8182	Intermediate Similarity	NPD6372	Approved
0.8073	Intermediate Similarity	NPD7128	Approved
0.8073	Intermediate Similarity	NPD6675	Approved
0.8073	Intermediate Similarity	NPD6402	Approved
0.8073	Intermediate Similarity	NPD5739	Approved
0.8036	Intermediate Similarity	NPD6649	Approved
0.8036	Intermediate Similarity	NPD6650	Approved
0.7928	Intermediate Similarity	NPD7320	Approved
0.7928	Intermediate Similarity	NPD6899	Approved
0.7928	Intermediate Similarity	NPD6881	Approved
0.7838	Intermediate Similarity	NPD5701	Approved
0.7838	Intermediate Similarity	NPD5697	Approved
0.7807	Intermediate Similarity	NPD8297	Approved
0.7807	Intermediate Similarity	NPD6882	Approved
0.7788	Intermediate Similarity	NPD7102	Approved
0.7788	Intermediate Similarity	NPD7290	Approved
0.7788	Intermediate Similarity	NPD6883	Approved
0.7778	Intermediate Similarity	NPD7640	Approved
0.7778	Intermediate Similarity	NPD7639	Approved
0.7768	Intermediate Similarity	NPD6011	Approved
0.7719	Intermediate Similarity	NPD6869	Approved
0.7719	Intermediate Similarity	NPD6847	Approved
0.7719	Intermediate Similarity	NPD8130	Phase 1
0.7719	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6617	Approved
0.7699	Intermediate Similarity	NPD6013	Approved
0.7699	Intermediate Similarity	NPD6014	Approved
0.7699	Intermediate Similarity	NPD6012	Approved
0.7685	Intermediate Similarity	NPD7638	Approved
0.7685	Intermediate Similarity	NPD5696	Approved
0.7664	Intermediate Similarity	NPD4697	Phase 3
0.7647	Intermediate Similarity	NPD6319	Approved
0.7636	Intermediate Similarity	NPD7632	Discontinued
0.7596	Intermediate Similarity	NPD5328	Approved
0.7593	Intermediate Similarity	NPD6083	Phase 2
0.7593	Intermediate Similarity	NPD6084	Phase 2
0.7589	Intermediate Similarity	NPD6008	Approved
0.7586	Intermediate Similarity	NPD4632	Approved
0.757	Intermediate Similarity	NPD5695	Phase 3
0.7547	Intermediate Similarity	NPD6399	Phase 3
0.7542	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5221	Approved
0.7477	Intermediate Similarity	NPD5211	Phase 2
0.7459	Intermediate Similarity	NPD7604	Phase 2
0.7458	Intermediate Similarity	NPD6868	Approved
0.7453	Intermediate Similarity	NPD6079	Approved
0.7438	Intermediate Similarity	NPD5983	Phase 2
0.7431	Intermediate Similarity	NPD4755	Approved
0.7431	Intermediate Similarity	NPD5173	Approved
0.7398	Intermediate Similarity	NPD7492	Approved
0.7395	Intermediate Similarity	NPD7115	Discovery
0.7355	Intermediate Similarity	NPD6059	Approved
0.7355	Intermediate Similarity	NPD6054	Approved
0.7345	Intermediate Similarity	NPD5141	Approved
0.7339	Intermediate Similarity	NPD6336	Discontinued
0.7339	Intermediate Similarity	NPD6616	Approved
0.7333	Intermediate Similarity	NPD6335	Approved
0.7323	Intermediate Similarity	NPD7260	Phase 2
0.7311	Intermediate Similarity	NPD6274	Approved
0.7308	Intermediate Similarity	NPD3618	Phase 1
0.7297	Intermediate Similarity	NPD4700	Approved
0.7297	Intermediate Similarity	NPD5285	Approved
0.7297	Intermediate Similarity	NPD4696	Approved
0.7297	Intermediate Similarity	NPD5286	Approved
0.728	Intermediate Similarity	NPD7078	Approved
0.728	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD7101	Approved
0.7273	Intermediate Similarity	NPD7100	Approved
0.7266	Intermediate Similarity	NPD6845	Suspended
0.725	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6317	Approved
0.7236	Intermediate Similarity	NPD6370	Approved
0.7232	Intermediate Similarity	NPD5223	Approved
0.7222	Intermediate Similarity	NPD7736	Approved
0.719	Intermediate Similarity	NPD6313	Approved
0.719	Intermediate Similarity	NPD6314	Approved
0.7179	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD8328	Phase 3
0.7168	Intermediate Similarity	NPD4633	Approved
0.7168	Intermediate Similarity	NPD5224	Approved
0.7168	Intermediate Similarity	NPD5225	Approved
0.7168	Intermediate Similarity	NPD5226	Approved
0.7156	Intermediate Similarity	NPD7748	Approved
0.7154	Intermediate Similarity	NPD6909	Approved
0.7154	Intermediate Similarity	NPD6015	Approved
0.7154	Intermediate Similarity	NPD6016	Approved
0.7154	Intermediate Similarity	NPD6908	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.713	Intermediate Similarity	NPD7515	Phase 2
0.713	Intermediate Similarity	NPD6050	Approved
0.713	Intermediate Similarity	NPD4767	Approved
0.713	Intermediate Similarity	NPD4768	Approved
0.7117	Intermediate Similarity	NPD7902	Approved
0.7115	Intermediate Similarity	NPD4786	Approved
0.7105	Intermediate Similarity	NPD5174	Approved
0.7105	Intermediate Similarity	NPD5175	Approved
0.7105	Intermediate Similarity	NPD4754	Approved
0.7103	Intermediate Similarity	NPD6904	Approved
0.7103	Intermediate Similarity	NPD6673	Approved
0.7103	Intermediate Similarity	NPD6080	Approved
0.7097	Intermediate Similarity	NPD5988	Approved
0.7094	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4629	Approved
0.7091	Intermediate Similarity	NPD5210	Approved
0.7064	Intermediate Similarity	NPD5778	Approved
0.7064	Intermediate Similarity	NPD5779	Approved
0.7063	Intermediate Similarity	NPD7507	Approved
0.7059	Intermediate Similarity	NPD6053	Discontinued
0.7037	Intermediate Similarity	NPD5692	Phase 3
0.7034	Intermediate Similarity	NPD4634	Approved
0.7016	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4729	Approved
0.7009	Intermediate Similarity	NPD4730	Approved
0.6981	Remote Similarity	NPD7521	Approved
0.6981	Remote Similarity	NPD5330	Approved
0.6981	Remote Similarity	NPD6409	Approved
0.6981	Remote Similarity	NPD6684	Approved
0.6981	Remote Similarity	NPD7334	Approved
0.6981	Remote Similarity	NPD7146	Approved
0.6972	Remote Similarity	NPD5693	Phase 1
0.6972	Remote Similarity	NPD8035	Phase 2
0.6972	Remote Similarity	NPD5694	Approved
0.6972	Remote Similarity	NPD8034	Phase 2
0.6953	Remote Similarity	NPD6033	Approved
0.6944	Remote Similarity	NPD4753	Phase 2
0.6937	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3667	Approved
0.6909	Remote Similarity	NPD4202	Approved
0.6899	Remote Similarity	NPD7319	Approved
0.6891	Remote Similarity	NPD5248	Approved
0.6891	Remote Similarity	NPD5251	Approved
0.6891	Remote Similarity	NPD5249	Phase 3
0.6891	Remote Similarity	NPD5250	Approved
0.6891	Remote Similarity	NPD5247	Approved
0.6887	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5128	Approved
0.6864	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5168	Approved
0.6863	Remote Similarity	NPD6115	Approved
0.6863	Remote Similarity	NPD6697	Approved
0.6863	Remote Similarity	NPD6118	Approved
0.6863	Remote Similarity	NPD6114	Approved
0.6863	Remote Similarity	NPD3617	Approved
0.6852	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6903	Approved
0.6847	Remote Similarity	NPD7900	Approved
0.6847	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6098	Approved
0.6818	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD5284	Approved
0.6818	Remote Similarity	NPD5281	Approved
0.6792	Remote Similarity	NPD3665	Phase 1
0.6792	Remote Similarity	NPD3666	Approved
0.6792	Remote Similarity	NPD3133	Approved
0.6789	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5654	Approved
0.678	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD4225	Approved
0.675	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5135	Approved
0.675	Remote Similarity	NPD5169	Approved
0.6729	Remote Similarity	NPD1694	Approved
0.6729	Remote Similarity	NPD5329	Approved
0.6723	Remote Similarity	NPD6686	Approved
0.6694	Remote Similarity	NPD5217	Approved
0.6694	Remote Similarity	NPD5215	Approved
0.6694	Remote Similarity	NPD5216	Approved
0.6694	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7637	Suspended
0.6639	Remote Similarity	NPD6614	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD4197	Approved
0.6618	Remote Similarity	NPD6333	Approved
0.6618	Remote Similarity	NPD6334	Approved
0.6606	Remote Similarity	NPD3573	Approved
0.6602	Remote Similarity	NPD6116	Phase 1
0.6577	Remote Similarity	NPD5207	Approved
0.6577	Remote Similarity	NPD5785	Approved
0.6569	Remote Similarity	NPD3703	Phase 2
0.6549	Remote Similarity	NPD6001	Approved
0.6538	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5167	Approved
0.6514	Remote Similarity	NPD5786	Approved
0.6508	Remote Similarity	NPD7328	Approved
0.6508	Remote Similarity	NPD7327	Approved
0.6484	Remote Similarity	NPD8033	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