NPASS Compound

Structure

NPC473039 OpenBabel07101719252D 33 37 0 0 1 0 0 0 0 0999 V2000 -7.5296 -1.3031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0296 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4315 -2.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1117 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5600 -0.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1635 -3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2975 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1635 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3630 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6994 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2975 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5655 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1635 -1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9563 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0296 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3576 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4315 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4315 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0296 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2975 -2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6994 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5655 -0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2975 0.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5655 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8956 -3.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0267 1.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 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 23 1 0 0 0 0 2 23 1 0 0 0 0 4 25 1 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 24 1 0 0 0 0 10 26 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 22 1 0 0 0 0 14 28 2 0 0 0 0 15 21 1 0 0 0 0 15 29 2 0 0 0 0 16 23 1 0 0 0 0 16 24 1 6 0 0 0 17 25 1 6 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 18 30 2 0 0 0 0 19 27 1 0 0 0 0 19 31 2 0 0 0 0 20 32 2 0 0 0 0 20 33 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 22 27 1 0 0 0 0 24 3 1 6 0 0 0 25 27 1 6 0 0 0 26 5 1 6 0 0 0 26 33 1 0 0 0 0 27 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.24
Volume:	469.688
LogP:	2.186
LogD:	1.516
LogS:	-4.578
# Rotatable Bonds:	1
TPSA:	94.58
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	5.156
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.203
MDCK Permeability:	2.8827591449953616e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.513
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	71.59864807128906%
Volume Distribution (VD):	0.358
Pgp-substrate:	21.952320098876953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	7.1
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.197
Skin Sensitization:	0.032
Carcinogencity:	0.701
Eye Corrosion:	0.101
Eye Irritation:	0.075
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC473039

Natural Product ID:	NPC473039
*Common Name:**	OLACLXTZQVYOIP-LJANSZIASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OLACLXTZQVYOIP-LJANSZIASA-N
Standard InCHI:	InChI=1S/C27H34O6/c1-23(2)16-11-14(28)22-21(24(16,3)9-7-18(23)30)15(29)13-25(4)17(12-19(31)27(22,25)6)26(5)10-8-20(32)33-26/h16-17H,7-13H2,1-6H3/t16-,17-,24-,25+,26-,27-/m0/s1
SMILES:	O=C1CC[C@@](O1)(C)[C@H]1CC(=O)[C@@]2([C@]1(C)CC(=O)C1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3601516
PubChem CID:	n.a.
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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1648	Individual Protein	Oligo-1,6-glucosidase	Saccharomyces cerevisiae S288c	IC50	=	81800.0	nM	PMID[551656]

☑ 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 NPC473039 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	252
0.1-0.2	1894
0.2-0.3	8966
0.3-0.4	14207
0.4-0.5	7536
0.5-0.6	6754
0.6-0.7	2662
0.7-0.8	384
0.8-0.85	32
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC271784
0.9048	High Similarity	NPC469561
0.8837	High Similarity	NPC473038
0.8721	High Similarity	NPC209882
0.8602	High Similarity	NPC216904
0.8571	High Similarity	NPC472226
0.8571	High Similarity	NPC472225
0.8511	High Similarity	NPC112753
0.8511	High Similarity	NPC275439
0.8506	High Similarity	NPC320801
0.8495	Intermediate Similarity	NPC125622
0.8478	Intermediate Similarity	NPC56525
0.8469	Intermediate Similarity	NPC473037
0.8404	Intermediate Similarity	NPC106557
0.8404	Intermediate Similarity	NPC23680
0.8404	Intermediate Similarity	NPC121339
0.8387	Intermediate Similarity	NPC241156
0.8387	Intermediate Similarity	NPC255809
0.8333	Intermediate Similarity	NPC124211
0.8298	Intermediate Similarity	NPC243525
0.8298	Intermediate Similarity	NPC40765
0.8298	Intermediate Similarity	NPC3772
0.8295	Intermediate Similarity	NPC109512
0.8276	Intermediate Similarity	NPC327969
0.8276	Intermediate Similarity	NPC321289
0.8261	Intermediate Similarity	NPC150383
0.8247	Intermediate Similarity	NPC53222
0.8229	Intermediate Similarity	NPC88198
0.8202	Intermediate Similarity	NPC311702
0.8202	Intermediate Similarity	NPC470223
0.8202	Intermediate Similarity	NPC11711
0.8202	Intermediate Similarity	NPC94531
0.8202	Intermediate Similarity	NPC123319
0.8191	Intermediate Similarity	NPC37646
0.8172	Intermediate Similarity	NPC25750
0.8163	Intermediate Similarity	NPC33973
0.8163	Intermediate Similarity	NPC70967
0.809	Intermediate Similarity	NPC100391
0.8085	Intermediate Similarity	NPC184870
0.8081	Intermediate Similarity	NPC216245
0.8081	Intermediate Similarity	NPC470251
0.8081	Intermediate Similarity	NPC135854
0.8081	Intermediate Similarity	NPC2436
0.8068	Intermediate Similarity	NPC240302
0.8043	Intermediate Similarity	NPC305039
0.8041	Intermediate Similarity	NPC157787
0.8041	Intermediate Similarity	NPC51370
0.8039	Intermediate Similarity	NPC272898
0.8039	Intermediate Similarity	NPC473036
0.8021	Intermediate Similarity	NPC292133
0.8021	Intermediate Similarity	NPC226986
0.798	Intermediate Similarity	NPC36321
0.7979	Intermediate Similarity	NPC470254
0.7978	Intermediate Similarity	NPC470015
0.7978	Intermediate Similarity	NPC168188
0.7952	Intermediate Similarity	NPC223187
0.7935	Intermediate Similarity	NPC28227
0.7931	Intermediate Similarity	NPC118987
0.7917	Intermediate Similarity	NPC95565
0.7895	Intermediate Similarity	NPC472223
0.7895	Intermediate Similarity	NPC472224
0.7879	Intermediate Similarity	NPC56498
0.7879	Intermediate Similarity	NPC281702
0.7872	Intermediate Similarity	NPC107690
0.7872	Intermediate Similarity	NPC218301
0.7865	Intermediate Similarity	NPC100297
0.7865	Intermediate Similarity	NPC133391
0.7857	Intermediate Similarity	NPC299971
0.7857	Intermediate Similarity	NPC307954
0.7857	Intermediate Similarity	NPC287833
0.7857	Intermediate Similarity	NPC205899
0.7857	Intermediate Similarity	NPC144660
0.7841	Intermediate Similarity	NPC474956
0.7841	Intermediate Similarity	NPC170038
0.7835	Intermediate Similarity	NPC43747
0.7826	Intermediate Similarity	NPC136948
0.7826	Intermediate Similarity	NPC99909
0.7826	Intermediate Similarity	NPC167877
0.7816	Intermediate Similarity	NPC469996
0.7812	Intermediate Similarity	NPC317586
0.7812	Intermediate Similarity	NPC470016
0.7812	Intermediate Similarity	NPC171395
0.7766	Intermediate Similarity	NPC289213
0.7755	Intermediate Similarity	NPC10364
0.7755	Intermediate Similarity	NPC271387
0.7755	Intermediate Similarity	NPC153792
0.7755	Intermediate Similarity	NPC16021
0.7753	Intermediate Similarity	NPC38350
0.7753	Intermediate Similarity	NPC477372
0.7753	Intermediate Similarity	NPC201912
0.7753	Intermediate Similarity	NPC232625
0.7745	Intermediate Similarity	NPC220974
0.7742	Intermediate Similarity	NPC190718
0.7732	Intermediate Similarity	NPC111684
0.7732	Intermediate Similarity	NPC328371
0.7732	Intermediate Similarity	NPC322063
0.7732	Intermediate Similarity	NPC58052
0.7723	Intermediate Similarity	NPC164835
0.7723	Intermediate Similarity	NPC228669
0.7723	Intermediate Similarity	NPC119493
0.7723	Intermediate Similarity	NPC255309
0.7717	Intermediate Similarity	NPC195640
0.7708	Intermediate Similarity	NPC318332
0.7708	Intermediate Similarity	NPC166906
0.7701	Intermediate Similarity	NPC475932
0.7684	Intermediate Similarity	NPC204341
0.7677	Intermediate Similarity	NPC316964
0.7667	Intermediate Similarity	NPC476458
0.7667	Intermediate Similarity	NPC258153
0.7667	Intermediate Similarity	NPC320514
0.7667	Intermediate Similarity	NPC260956
0.766	Intermediate Similarity	NPC469546
0.766	Intermediate Similarity	NPC173042
0.766	Intermediate Similarity	NPC262043
0.766	Intermediate Similarity	NPC285982
0.7653	Intermediate Similarity	NPC18319
0.7653	Intermediate Similarity	NPC122294
0.7647	Intermediate Similarity	NPC51452
0.7647	Intermediate Similarity	NPC96377
0.7647	Intermediate Similarity	NPC472935
0.764	Intermediate Similarity	NPC26139
0.7629	Intermediate Similarity	NPC174948
0.7629	Intermediate Similarity	NPC173875
0.7629	Intermediate Similarity	NPC473648
0.7629	Intermediate Similarity	NPC469995
0.7629	Intermediate Similarity	NPC318282
0.7624	Intermediate Similarity	NPC470954
0.7624	Intermediate Similarity	NPC236390
0.7624	Intermediate Similarity	NPC251017
0.7619	Intermediate Similarity	NPC115303
0.7609	Intermediate Similarity	NPC323765
0.7609	Intermediate Similarity	NPC29447
0.7609	Intermediate Similarity	NPC142649
0.7604	Intermediate Similarity	NPC79117
0.7596	Intermediate Similarity	NPC77947
0.7596	Intermediate Similarity	NPC286174
0.7582	Intermediate Similarity	NPC83569
0.7582	Intermediate Similarity	NPC477373
0.7582	Intermediate Similarity	NPC69279
0.7579	Intermediate Similarity	NPC478258
0.7579	Intermediate Similarity	NPC478257
0.7579	Intermediate Similarity	NPC20388
0.7576	Intermediate Similarity	NPC176845
0.7556	Intermediate Similarity	NPC147066
0.7551	Intermediate Similarity	NPC456
0.7551	Intermediate Similarity	NPC42042
0.7551	Intermediate Similarity	NPC328162
0.7551	Intermediate Similarity	NPC305483
0.7551	Intermediate Similarity	NPC96859
0.7551	Intermediate Similarity	NPC471775
0.7551	Intermediate Similarity	NPC7124
0.7551	Intermediate Similarity	NPC472941
0.7549	Intermediate Similarity	NPC28656
0.7549	Intermediate Similarity	NPC189616
0.7529	Intermediate Similarity	NPC197701
0.7528	Intermediate Similarity	NPC477371
0.7527	Intermediate Similarity	NPC471042
0.7527	Intermediate Similarity	NPC470345
0.7526	Intermediate Similarity	NPC471720
0.7526	Intermediate Similarity	NPC294266
0.7525	Intermediate Similarity	NPC308726
0.7525	Intermediate Similarity	NPC195290
0.7525	Intermediate Similarity	NPC204450
0.7525	Intermediate Similarity	NPC119601
0.7525	Intermediate Similarity	NPC234892
0.7524	Intermediate Similarity	NPC129689
0.7524	Intermediate Similarity	NPC470496
0.75	Intermediate Similarity	NPC297265
0.75	Intermediate Similarity	NPC472300
0.75	Intermediate Similarity	NPC295244
0.75	Intermediate Similarity	NPC476274
0.75	Intermediate Similarity	NPC120158
0.75	Intermediate Similarity	NPC475193
0.7477	Intermediate Similarity	NPC472929
0.7475	Intermediate Similarity	NPC475894
0.7475	Intermediate Similarity	NPC476253
0.7474	Intermediate Similarity	NPC474889
0.7474	Intermediate Similarity	NPC54689
0.7474	Intermediate Similarity	NPC474570
0.7473	Intermediate Similarity	NPC469325
0.7451	Intermediate Similarity	NPC55872
0.7451	Intermediate Similarity	NPC140723
0.7449	Intermediate Similarity	NPC469599
0.7449	Intermediate Similarity	NPC274417
0.7449	Intermediate Similarity	NPC297199
0.7447	Intermediate Similarity	NPC30421
0.7447	Intermediate Similarity	NPC476409
0.7431	Intermediate Similarity	NPC472934
0.7429	Intermediate Similarity	NPC304495
0.7426	Intermediate Similarity	NPC270155
0.7426	Intermediate Similarity	NPC473514
0.7426	Intermediate Similarity	NPC476223
0.7426	Intermediate Similarity	NPC310981
0.7426	Intermediate Similarity	NPC163372
0.7426	Intermediate Similarity	NPC476240
0.7426	Intermediate Similarity	NPC475867
0.7426	Intermediate Similarity	NPC224720
0.7426	Intermediate Similarity	NPC302537
0.7423	Intermediate Similarity	NPC243866
0.7423	Intermediate Similarity	NPC206810

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 NPC473039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	2371
0.2-0.3	4294
0.3-0.4	1566
0.4-0.5	336
0.5-0.6	174
0.6-0.7	145
0.7-0.8	40
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8352	Intermediate Similarity	NPD5207	Approved
0.8191	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6050	Approved
0.8043	Intermediate Similarity	NPD6904	Approved
0.8043	Intermediate Similarity	NPD6080	Approved
0.8043	Intermediate Similarity	NPD6673	Approved
0.7957	Intermediate Similarity	NPD5692	Phase 3
0.7935	Intermediate Similarity	NPD5737	Approved
0.7935	Intermediate Similarity	NPD6672	Approved
0.7895	Intermediate Similarity	NPD6001	Approved
0.7872	Intermediate Similarity	NPD5694	Approved
0.7755	Intermediate Similarity	NPD5696	Approved
0.7742	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD5208	Approved
0.7717	Intermediate Similarity	NPD7334	Approved
0.7717	Intermediate Similarity	NPD6098	Approved
0.7717	Intermediate Similarity	NPD7521	Approved
0.7717	Intermediate Similarity	NPD6409	Approved
0.7717	Intermediate Similarity	NPD6684	Approved
0.7717	Intermediate Similarity	NPD7146	Approved
0.7717	Intermediate Similarity	NPD5330	Approved
0.7684	Intermediate Similarity	NPD5693	Phase 1
0.7684	Intermediate Similarity	NPD5284	Approved
0.7684	Intermediate Similarity	NPD5281	Approved
0.7647	Intermediate Similarity	NPD6008	Approved
0.7629	Intermediate Similarity	NPD5695	Phase 3
0.7629	Intermediate Similarity	NPD5654	Approved
0.7624	Intermediate Similarity	NPD6052	Approved
0.7604	Intermediate Similarity	NPD6399	Phase 3
0.7553	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD5959	Approved
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7447	Intermediate Similarity	NPD3573	Approved
0.7429	Intermediate Similarity	NPD6372	Approved
0.7429	Intermediate Similarity	NPD6373	Approved
0.7404	Intermediate Similarity	NPD6614	Approved
0.7333	Intermediate Similarity	NPD7320	Approved
0.7308	Intermediate Similarity	NPD7128	Approved
0.7308	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD5739	Approved
0.7308	Intermediate Similarity	NPD6402	Approved
0.729	Intermediate Similarity	NPD6650	Approved
0.729	Intermediate Similarity	NPD6649	Approved
0.7283	Intermediate Similarity	NPD4223	Phase 3
0.7283	Intermediate Similarity	NPD4221	Approved
0.7234	Intermediate Similarity	NPD5329	Approved
0.7222	Intermediate Similarity	NPD3617	Approved
0.72	Intermediate Similarity	NPD7732	Phase 3
0.7174	Intermediate Similarity	NPD4139	Approved
0.7174	Intermediate Similarity	NPD4692	Approved
0.7172	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7900	Approved
0.717	Intermediate Similarity	NPD6881	Approved
0.717	Intermediate Similarity	NPD6899	Approved
0.7159	Intermediate Similarity	NPD5733	Approved
0.7158	Intermediate Similarity	NPD4694	Approved
0.7158	Intermediate Similarity	NPD5690	Phase 2
0.7158	Intermediate Similarity	NPD5280	Approved
0.7158	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4197	Approved
0.7113	Intermediate Similarity	NPD5328	Approved
0.71	Intermediate Similarity	NPD4629	Approved
0.71	Intermediate Similarity	NPD5210	Approved
0.7075	Intermediate Similarity	NPD5701	Approved
0.7075	Intermediate Similarity	NPD5697	Approved
0.7037	Intermediate Similarity	NPD6883	Approved
0.7037	Intermediate Similarity	NPD7102	Approved
0.7037	Intermediate Similarity	NPD7290	Approved
0.703	Intermediate Similarity	NPD4697	Phase 3
0.703	Intermediate Similarity	NPD7614	Phase 1
0.7011	Intermediate Similarity	NPD4747	Approved
0.7009	Intermediate Similarity	NPD6011	Approved
0.6979	Remote Similarity	NPD4138	Approved
0.6979	Remote Similarity	NPD4688	Approved
0.6979	Remote Similarity	NPD5205	Approved
0.6979	Remote Similarity	NPD4689	Approved
0.6979	Remote Similarity	NPD4693	Phase 3
0.6979	Remote Similarity	NPD4690	Approved
0.6972	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8130	Phase 1
0.6972	Remote Similarity	NPD6869	Approved
0.6972	Remote Similarity	NPD6847	Approved
0.6972	Remote Similarity	NPD6617	Approved
0.697	Remote Similarity	NPD6079	Approved
0.6966	Remote Similarity	NPD4687	Approved
0.6961	Remote Similarity	NPD7902	Approved
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6939	Remote Similarity	NPD4753	Phase 2
0.6939	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6081	Approved
0.6932	Remote Similarity	NPD5276	Approved
0.6909	Remote Similarity	NPD6882	Approved
0.6909	Remote Similarity	NPD8297	Approved
0.6897	Remote Similarity	NPD4137	Phase 3
0.6875	Remote Similarity	NPD1694	Approved
0.6832	Remote Similarity	NPD7748	Approved
0.6818	Remote Similarity	NPD4691	Approved
0.6804	Remote Similarity	NPD5279	Phase 3
0.6804	Remote Similarity	NPD3618	Phase 1
0.68	Remote Similarity	NPD8034	Phase 2
0.68	Remote Similarity	NPD8035	Phase 2
0.6796	Remote Similarity	NPD4755	Approved
0.6771	Remote Similarity	NPD3665	Phase 1
0.6771	Remote Similarity	NPD3133	Approved
0.6771	Remote Similarity	NPD4786	Approved
0.6771	Remote Similarity	NPD3666	Approved
0.6737	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5133	Approved
0.6724	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4096	Approved
0.6699	Remote Similarity	NPD5221	Approved
0.6699	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5222	Approved
0.6698	Remote Similarity	NPD5091	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6635	Remote Similarity	NPD5173	Approved
0.6634	Remote Similarity	NPD7515	Phase 2
0.6628	Remote Similarity	NPD7341	Phase 2
0.6609	Remote Similarity	NPD6335	Approved
0.6604	Remote Similarity	NPD5223	Approved
0.66	Remote Similarity	NPD6051	Approved
0.6598	Remote Similarity	NPD3668	Phase 3
0.6596	Remote Similarity	NPD4195	Approved
0.6593	Remote Similarity	NPD4058	Approved
0.6579	Remote Similarity	NPD6274	Approved
0.6579	Remote Similarity	NPD6868	Approved
0.6569	Remote Similarity	NPD4202	Approved
0.6562	Remote Similarity	NPD3667	Approved
0.6556	Remote Similarity	NPD5777	Approved
0.6555	Remote Similarity	NPD7492	Approved
0.6552	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD7100	Approved
0.6549	Remote Similarity	NPD4632	Approved
0.6542	Remote Similarity	NPD4633	Approved
0.6542	Remote Similarity	NPD5226	Approved
0.6542	Remote Similarity	NPD5224	Approved
0.6542	Remote Similarity	NPD5225	Approved
0.6542	Remote Similarity	NPD5211	Phase 2
0.6526	Remote Similarity	NPD4695	Discontinued
0.6522	Remote Similarity	NPD7115	Discovery
0.6522	Remote Similarity	NPD6317	Approved
0.6522	Remote Similarity	NPD3702	Approved
0.6509	Remote Similarity	NPD6404	Discontinued
0.65	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD4518	Approved
0.6496	Remote Similarity	NPD6059	Approved
0.6496	Remote Similarity	NPD6054	Approved
0.6495	Remote Similarity	NPD4788	Approved
0.6481	Remote Similarity	NPD5175	Approved
0.6481	Remote Similarity	NPD5174	Approved
0.6481	Remote Similarity	NPD4754	Approved
0.6471	Remote Similarity	NPD6411	Approved
0.6466	Remote Similarity	NPD6314	Approved
0.6466	Remote Similarity	NPD6313	Approved
0.6465	Remote Similarity	NPD4623	Approved
0.6465	Remote Similarity	NPD4519	Discontinued
0.646	Remote Similarity	NPD6053	Discontinued
0.6455	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8293	Discontinued
0.6446	Remote Similarity	NPD7078	Approved
0.6441	Remote Similarity	NPD6909	Approved
0.6441	Remote Similarity	NPD6908	Approved
0.6422	Remote Similarity	NPD5141	Approved
0.6415	Remote Similarity	NPD7638	Approved
0.6404	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7736	Approved
0.6387	Remote Similarity	NPD6370	Approved
0.6379	Remote Similarity	NPD6009	Approved
0.6364	Remote Similarity	NPD4224	Phase 2
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6319	Approved
0.6355	Remote Similarity	NPD7639	Approved
0.6355	Remote Similarity	NPD7640	Approved
0.6333	Remote Similarity	NPD7604	Phase 2
0.632	Remote Similarity	NPD6845	Suspended
0.6306	Remote Similarity	NPD6412	Phase 2
0.6303	Remote Similarity	NPD5983	Phase 2
0.6303	Remote Similarity	NPD6016	Approved
0.6303	Remote Similarity	NPD6015	Approved
0.6283	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD4730	Approved
0.6239	Remote Similarity	NPD7632	Discontinued
0.623	Remote Similarity	NPD6336	Discontinued
0.6224	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5360	Phase 3
0.6196	Remote Similarity	NPD4243	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