NPASS Compound

Structure

CID60350 OpenBabel06191715392D 34 38 0 0 1 0 0 0 0 0999 V2000 1.8874 -3.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7936 -5.9539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 2.9646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5679 2.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -1.9864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6931 1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3858 -0.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3855 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6928 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8471 -1.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4960 -2.6445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1448 -4.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8465 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5407 -2.4417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4469 -5.2279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 -3.5732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5404 -1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8471 1.4662 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8465 0.4890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5393 1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4022 -5.4307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6933 1.9547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -0.9765 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6933 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 0.4886 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 4.7534 -3.7760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4055 1.9653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7043 -6.3594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0555 -4.7047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 1 1 1 0 0 0 18 21 1 0 0 0 0 19 25 1 0 0 0 0 20 31 2 0 0 0 0 21 27 1 6 0 0 0 22 26 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	3.53
LogD:	3.227
LogS:	-3.043
# Rotatable Bonds:	2
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.851
Synthetic Accessibility Score:	3.377
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.296
MDCK Permeability:	2.195650631620083e-05
Pgp-inhibitor:	0.156
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.259
Plasma Protein Binding (PPB):	83.62210845947266%
Volume Distribution (VD):	1.712
Pgp-substrate:	18.349510192871094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.622
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.196
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.455
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.607

ADMET: Excretion

Clearance (CL):	11.817
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.302
Carcinogencity:	0.401
Eye Corrosion:	0.64
Eye Irritation:	0.895
Respiratory Toxicity:	0.362

Download Data

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

Natural Product: NPC60350

Natural Product ID:	NPC60350
*Common Name:**	PJYWFBGSJPGTAM-ACKRQZOBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PJYWFBGSJPGTAM-ACKRQZOBSA-N
Standard InCHI:	InChI=1S/C30H44O4/c1-18(15-20(31)16-19(2)25(33)34)21-9-11-28(6)23-8-7-22-26(3,4)24(32)10-12-29(22)17-30(23,29)14-13-27(21,28)5/h16,18,21-23H,7-15,17H2,1-6H3,(H,33,34)/b19-16+/t18-,21-,22+,23+,27-,28+,29-,30+/m1/s1
SMILES:	O=C(/C=C(/C(=O)O)C)C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CCC(=O)C2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519222
PubChem CID:	21593999
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346966]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	tuber	n.a.	PMID[15180301]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	leaves,?stems	USA	n.a.	PMID[16124770]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17381154]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23668986]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25843525]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760078]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20262	Delia paludosa	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22563	Sclerocarya birrea	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21914	Turnera angustifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22700	Dacrydium comosum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20328	Plumeria acutifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21090	Chrysanthemum ornatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20772	Pedalium murex	Species	Pedaliaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	LC50	=	1700.0	nM	PMID[465077]

☑ 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 NPC60350 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	165
0.1-0.2	1458
0.2-0.3	7417
0.3-0.4	15349
0.4-0.5	7225
0.5-0.6	6889
0.6-0.7	3564
0.7-0.8	551
0.8-0.85	52
0.85-0.9	19
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC16287
0.9873	High Similarity	NPC178025
0.9873	High Similarity	NPC181743
0.9512	High Similarity	NPC476293
0.9375	High Similarity	NPC472239
0.9294	High Similarity	NPC23217
0.9136	High Similarity	NPC3511
0.9136	High Similarity	NPC472867
0.9136	High Similarity	NPC142253
0.9036	High Similarity	NPC8571
0.9024	High Similarity	NPC279639
0.9024	High Similarity	NPC3856
0.8977	High Similarity	NPC476174
0.8941	High Similarity	NPC117122
0.8929	High Similarity	NPC186975
0.8916	High Similarity	NPC87552
0.8902	High Similarity	NPC469799
0.8902	High Similarity	NPC469804
0.8902	High Similarity	NPC469805
0.8902	High Similarity	NPC469806
0.8876	High Similarity	NPC29152
0.8824	High Similarity	NPC236618
0.8778	High Similarity	NPC156546
0.8734	High Similarity	NPC469803
0.8659	High Similarity	NPC469797
0.8659	High Similarity	NPC469798
0.8621	High Similarity	NPC262043
0.8621	High Similarity	NPC66344
0.8605	High Similarity	NPC136948
0.8519	High Similarity	NPC91665
0.85	High Similarity	NPC255650
0.8488	Intermediate Similarity	NPC472869
0.8471	Intermediate Similarity	NPC248758
0.8471	Intermediate Similarity	NPC19849
0.8471	Intermediate Similarity	NPC164577
0.8471	Intermediate Similarity	NPC472864
0.8452	Intermediate Similarity	NPC320514
0.8427	Intermediate Similarity	NPC470113
0.8395	Intermediate Similarity	NPC69408
0.8375	Intermediate Similarity	NPC255021
0.8372	Intermediate Similarity	NPC29447
0.8354	Intermediate Similarity	NPC133253
0.8354	Intermediate Similarity	NPC21944
0.8353	Intermediate Similarity	NPC97913
0.8295	Intermediate Similarity	NPC472870
0.8272	Intermediate Similarity	NPC476346
0.8256	Intermediate Similarity	NPC472865
0.825	Intermediate Similarity	NPC180015
0.825	Intermediate Similarity	NPC474228
0.825	Intermediate Similarity	NPC109576
0.825	Intermediate Similarity	NPC56747
0.825	Intermediate Similarity	NPC130016
0.825	Intermediate Similarity	NPC303613
0.8228	Intermediate Similarity	NPC214770
0.8228	Intermediate Similarity	NPC477856
0.8222	Intermediate Similarity	NPC474018
0.8222	Intermediate Similarity	NPC476187
0.8222	Intermediate Similarity	NPC473986
0.8222	Intermediate Similarity	NPC204341
0.8161	Intermediate Similarity	NPC11711
0.8161	Intermediate Similarity	NPC472940
0.8161	Intermediate Similarity	NPC472931
0.8161	Intermediate Similarity	NPC269638
0.8152	Intermediate Similarity	NPC293052
0.814	Intermediate Similarity	NPC472740
0.814	Intermediate Similarity	NPC474790
0.814	Intermediate Similarity	NPC470015
0.814	Intermediate Similarity	NPC168188
0.814	Intermediate Similarity	NPC474976
0.814	Intermediate Similarity	NPC41539
0.8132	Intermediate Similarity	NPC476304
0.8118	Intermediate Similarity	NPC147066
0.8118	Intermediate Similarity	NPC477372
0.8118	Intermediate Similarity	NPC278459
0.8111	Intermediate Similarity	NPC472866
0.8101	Intermediate Similarity	NPC477857
0.8095	Intermediate Similarity	NPC158846
0.8085	Intermediate Similarity	NPC98868
0.8068	Intermediate Similarity	NPC70661
0.8065	Intermediate Similarity	NPC456
0.8065	Intermediate Similarity	NPC472941
0.8049	Intermediate Similarity	NPC293803
0.8046	Intermediate Similarity	NPC194937
0.8046	Intermediate Similarity	NPC476038
0.8043	Intermediate Similarity	NPC476186
0.8025	Intermediate Similarity	NPC251705
0.8022	Intermediate Similarity	NPC110923
0.8022	Intermediate Similarity	NPC74296
0.8	Intermediate Similarity	NPC159577
0.8	Intermediate Similarity	NPC265782
0.8	Intermediate Similarity	NPC282593
0.8	Intermediate Similarity	NPC2634
0.8	Intermediate Similarity	NPC251929
0.8	Intermediate Similarity	NPC35734
0.8	Intermediate Similarity	NPC307176
0.7978	Intermediate Similarity	NPC163016
0.7978	Intermediate Similarity	NPC128644
0.7978	Intermediate Similarity	NPC476409
0.7978	Intermediate Similarity	NPC75315
0.7976	Intermediate Similarity	NPC198240
0.7955	Intermediate Similarity	NPC123319
0.7955	Intermediate Similarity	NPC311702
0.7955	Intermediate Similarity	NPC94531
0.7955	Intermediate Similarity	NPC283733
0.7935	Intermediate Similarity	NPC472871
0.7931	Intermediate Similarity	NPC49019
0.7931	Intermediate Similarity	NPC167103
0.7927	Intermediate Similarity	NPC474796
0.7927	Intermediate Similarity	NPC309852
0.7927	Intermediate Similarity	NPC329866
0.7927	Intermediate Similarity	NPC474797
0.7907	Intermediate Similarity	NPC201912
0.7907	Intermediate Similarity	NPC4166
0.7907	Intermediate Similarity	NPC471898
0.7907	Intermediate Similarity	NPC38350
0.7901	Intermediate Similarity	NPC115023
0.7901	Intermediate Similarity	NPC54123
0.7901	Intermediate Similarity	NPC305501
0.7901	Intermediate Similarity	NPC234707
0.7895	Intermediate Similarity	NPC197386
0.7895	Intermediate Similarity	NPC235464
0.7895	Intermediate Similarity	NPC166745
0.7889	Intermediate Similarity	NPC48107
0.7882	Intermediate Similarity	NPC190211
0.7882	Intermediate Similarity	NPC215843
0.7882	Intermediate Similarity	NPC477371
0.7875	Intermediate Similarity	NPC139397
0.7872	Intermediate Similarity	NPC301534
0.7872	Intermediate Similarity	NPC250757
0.7872	Intermediate Similarity	NPC114743
0.7872	Intermediate Similarity	NPC195366
0.7857	Intermediate Similarity	NPC61952
0.7857	Intermediate Similarity	NPC471035
0.7857	Intermediate Similarity	NPC212661
0.7849	Intermediate Similarity	NPC124207
0.7841	Intermediate Similarity	NPC96095
0.7826	Intermediate Similarity	NPC473998
0.7816	Intermediate Similarity	NPC311092
0.7816	Intermediate Similarity	NPC133391
0.7816	Intermediate Similarity	NPC260956
0.7812	Intermediate Similarity	NPC470074
0.7812	Intermediate Similarity	NPC287833
0.7805	Intermediate Similarity	NPC470045
0.7805	Intermediate Similarity	NPC470044
0.7802	Intermediate Similarity	NPC214387
0.7802	Intermediate Similarity	NPC309603
0.7802	Intermediate Similarity	NPC473999
0.7802	Intermediate Similarity	NPC474844
0.7791	Intermediate Similarity	NPC474509
0.7789	Intermediate Similarity	NPC253826
0.7789	Intermediate Similarity	NPC476253
0.7778	Intermediate Similarity	NPC260040
0.7778	Intermediate Similarity	NPC93778
0.7778	Intermediate Similarity	NPC40574
0.7778	Intermediate Similarity	NPC96496
0.7766	Intermediate Similarity	NPC174948
0.7766	Intermediate Similarity	NPC33473
0.7766	Intermediate Similarity	NPC173875
0.7766	Intermediate Similarity	NPC171395
0.7766	Intermediate Similarity	NPC318282
0.7766	Intermediate Similarity	NPC469995
0.7765	Intermediate Similarity	NPC82635
0.7765	Intermediate Similarity	NPC105197
0.7753	Intermediate Similarity	NPC474537
0.7753	Intermediate Similarity	NPC142649
0.7753	Intermediate Similarity	NPC471224
0.775	Intermediate Similarity	NPC20610
0.7742	Intermediate Similarity	NPC474736
0.7738	Intermediate Similarity	NPC246445
0.7738	Intermediate Similarity	NPC19907
0.7738	Intermediate Similarity	NPC474463
0.7738	Intermediate Similarity	NPC20466
0.7738	Intermediate Similarity	NPC180886
0.7732	Intermediate Similarity	NPC472924
0.7732	Intermediate Similarity	NPC99411
0.7732	Intermediate Similarity	NPC118174
0.7727	Intermediate Similarity	NPC215893
0.7727	Intermediate Similarity	NPC83569
0.7727	Intermediate Similarity	NPC69279
0.7727	Intermediate Similarity	NPC477373
0.7722	Intermediate Similarity	NPC189917
0.7722	Intermediate Similarity	NPC168824
0.7722	Intermediate Similarity	NPC107704
0.7722	Intermediate Similarity	NPC39462
0.7722	Intermediate Similarity	NPC96812
0.7717	Intermediate Similarity	NPC477149
0.7717	Intermediate Similarity	NPC48010
0.7717	Intermediate Similarity	NPC477147
0.7711	Intermediate Similarity	NPC20025
0.7692	Intermediate Similarity	NPC72397
0.7684	Intermediate Similarity	NPC328371
0.7683	Intermediate Similarity	NPC5701
0.7674	Intermediate Similarity	NPC192744
0.766	Intermediate Similarity	NPC8993
0.7654	Intermediate Similarity	NPC182815
0.7653	Intermediate Similarity	NPC293753
0.7647	Intermediate Similarity	NPC470557
0.7647	Intermediate Similarity	NPC66105
0.7647	Intermediate Similarity	NPC97377
0.7647	Intermediate Similarity	NPC165711

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 NPC60350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1676
0.2-0.3	4398
0.3-0.4	2094
0.4-0.5	433
0.5-0.6	180
0.6-0.7	170
0.7-0.8	54
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
0.8	Intermediate Similarity	NPD4747	Approved
0.8	Intermediate Similarity	NPD4691	Approved
0.7875	Intermediate Similarity	NPD4137	Phase 3
0.7711	Intermediate Similarity	NPD5733	Approved
0.7711	Intermediate Similarity	NPD4058	Approved
0.7614	Intermediate Similarity	NPD4221	Approved
0.7614	Intermediate Similarity	NPD4223	Phase 3
0.7556	Intermediate Similarity	NPD5329	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD4687	Approved
0.747	Intermediate Similarity	NPD5276	Approved
0.7447	Intermediate Similarity	NPD5281	Approved
0.7447	Intermediate Similarity	NPD5284	Approved
0.7444	Intermediate Similarity	NPD4197	Approved
0.7423	Intermediate Similarity	NPD6083	Phase 2
0.7423	Intermediate Similarity	NPD6084	Phase 2
0.7419	Intermediate Similarity	NPD6673	Approved
0.7419	Intermediate Similarity	NPD6904	Approved
0.7419	Intermediate Similarity	NPD6080	Approved
0.7396	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6399	Phase 3
0.7356	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7146	Approved
0.7283	Intermediate Similarity	NPD4138	Approved
0.7283	Intermediate Similarity	NPD4689	Approved
0.7283	Intermediate Similarity	NPD4690	Approved
0.7283	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6409	Approved
0.7283	Intermediate Similarity	NPD7521	Approved
0.7283	Intermediate Similarity	NPD4623	Approved
0.7283	Intermediate Similarity	NPD4688	Approved
0.7283	Intermediate Similarity	NPD5330	Approved
0.7283	Intermediate Similarity	NPD4693	Phase 3
0.7283	Intermediate Similarity	NPD5205	Approved
0.7283	Intermediate Similarity	NPD4519	Discontinued
0.7283	Intermediate Similarity	NPD7334	Approved
0.7283	Intermediate Similarity	NPD6684	Approved
0.7283	Intermediate Similarity	NPD5690	Phase 2
0.7273	Intermediate Similarity	NPD7640	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7273	Intermediate Similarity	NPD6404	Discontinued
0.7263	Intermediate Similarity	NPD5693	Phase 1
0.7263	Intermediate Similarity	NPD6079	Approved
0.7263	Intermediate Similarity	NPD7515	Phase 2
0.7253	Intermediate Similarity	NPD3666	Approved
0.7253	Intermediate Similarity	NPD3133	Approved
0.7253	Intermediate Similarity	NPD4786	Approved
0.7253	Intermediate Similarity	NPD3665	Phase 1
0.7234	Intermediate Similarity	NPD5328	Approved
0.7234	Intermediate Similarity	NPD4753	Phase 2
0.7234	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5695	Phase 3
0.7191	Intermediate Similarity	NPD4695	Discontinued
0.7172	Intermediate Similarity	NPD7638	Approved
0.7172	Intermediate Similarity	NPD5696	Approved
0.7159	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD4788	Approved
0.7128	Intermediate Similarity	NPD5208	Approved
0.7128	Intermediate Similarity	NPD6903	Approved
0.7113	Intermediate Similarity	NPD6001	Approved
0.7113	Intermediate Similarity	NPD7748	Approved
0.7097	Intermediate Similarity	NPD4694	Approved
0.7097	Intermediate Similarity	NPD5280	Approved
0.7097	Intermediate Similarity	NPD6098	Approved
0.7097	Intermediate Similarity	NPD3618	Phase 1
0.7083	Intermediate Similarity	NPD6050	Approved
0.7079	Intermediate Similarity	NPD4195	Approved
0.7064	Intermediate Similarity	NPD7115	Discovery
0.7041	Intermediate Similarity	NPD4629	Approved
0.7041	Intermediate Similarity	NPD5210	Approved
0.7033	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3667	Approved
0.6989	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5692	Phase 3
0.697	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7614	Phase 1
0.697	Remote Similarity	NPD5221	Approved
0.697	Remote Similarity	NPD5222	Approved
0.6961	Remote Similarity	NPD5211	Phase 2
0.6952	Remote Similarity	NPD6881	Approved
0.6952	Remote Similarity	NPD6899	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6915	Remote Similarity	NPD5279	Phase 3
0.6907	Remote Similarity	NPD5694	Approved
0.69	Remote Similarity	NPD7902	Approved
0.69	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD6081	Approved
0.6857	Remote Similarity	NPD5697	Approved
0.6837	Remote Similarity	NPD4202	Approved
0.6837	Remote Similarity	NPD5133	Approved
0.6827	Remote Similarity	NPD5141	Approved
0.6822	Remote Similarity	NPD7102	Approved
0.6822	Remote Similarity	NPD7290	Approved
0.6822	Remote Similarity	NPD6883	Approved
0.6809	Remote Similarity	NPD5363	Approved
0.6804	Remote Similarity	NPD5207	Approved
0.6804	Remote Similarity	NPD5785	Approved
0.68	Remote Similarity	NPD4697	Phase 3
0.6792	Remote Similarity	NPD7320	Approved
0.6792	Remote Similarity	NPD6011	Approved
0.6774	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5285	Approved
0.6765	Remote Similarity	NPD5286	Approved
0.6765	Remote Similarity	NPD4696	Approved
0.6759	Remote Similarity	NPD6617	Approved
0.6759	Remote Similarity	NPD6869	Approved
0.6759	Remote Similarity	NPD6649	Approved
0.6759	Remote Similarity	NPD6847	Approved
0.6759	Remote Similarity	NPD6650	Approved
0.6759	Remote Similarity	NPD8130	Phase 1
0.6739	Remote Similarity	NPD8028	Phase 2
0.6735	Remote Similarity	NPD8034	Phase 2
0.6735	Remote Similarity	NPD8035	Phase 2
0.6735	Remote Similarity	NPD7637	Suspended
0.6733	Remote Similarity	NPD4755	Approved
0.6733	Remote Similarity	NPD5959	Approved
0.6729	Remote Similarity	NPD6373	Approved
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6372	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6702	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD5223	Approved
0.6698	Remote Similarity	NPD5701	Approved
0.6697	Remote Similarity	NPD8297	Approved
0.6697	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4224	Phase 2
0.6667	Remote Similarity	NPD3573	Approved
0.6635	Remote Similarity	NPD5224	Approved
0.6635	Remote Similarity	NPD4633	Approved
0.6635	Remote Similarity	NPD5091	Approved
0.6635	Remote Similarity	NPD7632	Discontinued
0.6635	Remote Similarity	NPD5226	Approved
0.6635	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD4096	Approved
0.6606	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4700	Approved
0.66	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7900	Approved
0.6596	Remote Similarity	NPD5362	Discontinued
0.6571	Remote Similarity	NPD6052	Approved
0.6571	Remote Similarity	NPD5174	Approved
0.6571	Remote Similarity	NPD5175	Approved
0.6559	Remote Similarity	NPD4139	Approved
0.6559	Remote Similarity	NPD4692	Approved
0.6542	Remote Similarity	NPD6614	Approved
0.6535	Remote Similarity	NPD5654	Approved
0.6518	Remote Similarity	NPD6868	Approved
0.6489	Remote Similarity	NPD4270	Approved
0.6489	Remote Similarity	NPD4269	Approved
0.6486	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD6686	Approved
0.6477	Remote Similarity	NPD4243	Approved
0.6471	Remote Similarity	NPD7732	Phase 3
0.6452	Remote Similarity	NPD7525	Registered
0.6452	Remote Similarity	NPD4252	Approved
0.6449	Remote Similarity	NPD6008	Approved
0.6429	Remote Similarity	NPD4518	Approved
0.6415	Remote Similarity	NPD4754	Approved
0.641	Remote Similarity	NPD7604	Phase 2
0.6404	Remote Similarity	NPD6335	Approved
0.6389	Remote Similarity	NPD6412	Phase 2
0.6386	Remote Similarity	NPD4194	Approved
0.6386	Remote Similarity	NPD4193	Approved
0.6386	Remote Similarity	NPD4191	Approved
0.6386	Remote Similarity	NPD4192	Approved
0.6383	Remote Similarity	NPD6902	Approved
0.6374	Remote Similarity	NPD6117	Approved
0.6372	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.6348	Remote Similarity	NPD7100	Approved
0.6348	Remote Similarity	NPD7101	Approved
0.6346	Remote Similarity	NPD4225	Approved
0.6333	Remote Similarity	NPD4785	Approved
0.6333	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4784	Approved
0.633	Remote Similarity	NPD5128	Approved
0.633	Remote Similarity	NPD4730	Approved
0.633	Remote Similarity	NPD4729	Approved
0.633	Remote Similarity	NPD5168	Approved
0.6322	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD5360	Phase 3
0.6316	Remote Similarity	NPD6009	Approved
0.6316	Remote Similarity	NPD6317	Approved
0.6304	Remote Similarity	NPD6116	Phase 1
0.6296	Remote Similarity	NPD4767	Approved
0.6296	Remote Similarity	NPD4768	Approved
0.6289	Remote Similarity	NPD1696	Phase 3
0.6289	Remote Similarity	NPD1694	Approved
0.6264	Remote Similarity	NPD6942	Approved
0.6264	Remote Similarity	NPD7339	Approved
0.6261	Remote Similarity	NPD6313	Approved
0.6261	Remote Similarity	NPD6314	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