NPASS Compound

Structure

CID101991 OpenBabel06191715442D 47 54 0 0 1 0 0 0 0 0999 V2000 -5.0447 -0.5514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0643 -2.1892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8415 4.2549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6360 -1.3873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7010 -0.3002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1738 -1.1190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0951 1.4009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1731 -2.2119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2834 1.8754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3362 -2.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8188 -3.0592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6504 2.8379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0203 2.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4403 1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1229 0.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6283 0.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7555 -1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2733 -0.0049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5817 -1.3760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8377 3.3111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7555 -0.3002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4403 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7010 -1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0900 0.4608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4667 1.4097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2274 -2.2233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6511 1.8877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0060 1.8981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7992 -1.4213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7645 -3.0478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6283 1.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2591 0.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2828 -1.1190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4616 0.4695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8162 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8162 1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8338 1.4206 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7448 -1.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8222 0.4699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1738 -2.7567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9063 -0.0164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2471 -3.8611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6283 2.8426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2078 -0.5854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3579 -0.9225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6443 0.0024 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 8 1 0 0 0 0 4 19 2 0 0 0 0 5 6 2 0 0 0 0 5 21 1 0 0 0 0 6 23 1 0 0 0 0 7 9 2 0 0 0 0 7 24 1 0 0 0 0 8 26 1 0 0 0 0 9 25 1 0 0 0 0 10 11 2 0 0 0 0 10 29 1 0 0 0 0 11 30 1 0 0 0 0 12 20 1 0 0 0 0 13 20 2 0 0 0 0 14 22 2 0 0 0 0 14 31 1 0 0 0 0 15 21 1 0 0 0 0 15 32 2 0 0 0 0 16 22 1 0 0 0 0 16 35 2 0 0 0 0 17 23 2 0 0 0 0 17 33 1 0 0 0 0 18 24 2 0 0 0 0 18 34 1 0 0 0 0 21 33 2 0 0 0 0 22 32 1 0 0 0 0 23 40 1 0 0 0 0 24 41 1 0 0 0 0 25 27 1 0 0 0 0 25 34 2 0 0 0 0 26 30 2 0 0 0 0 26 38 1 0 0 0 0 27 12 1 6 0 0 0 27 37 1 0 0 0 0 28 13 1 1 0 0 0 28 36 1 0 0 0 0 28 37 1 0 0 0 0 29 38 2 0 0 0 0 30 42 1 0 0 0 0 31 36 2 0 0 0 0 31 43 1 0 0 0 0 32 45 1 0 0 0 0 33 45 1 0 0 0 0 34 46 1 0 0 0 0 35 36 1 0 0 0 0 35 47 1 0 0 0 0 37 39 1 1 0 0 0 38 44 1 0 0 0 0 39 29 1 6 0 0 0 39 46 1 0 0 0 0 39 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	630.23
Volume:	645.423
LogP:	8.32
LogD:	4.47
LogS:	-1.409
# Rotatable Bonds:	4
TPSA:	132.75
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	4.779
Fsp3:	0.231
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.491
MDCK Permeability:	1.0580276466498617e-05
Pgp-inhibitor:	0.802
Pgp-substrate:	0.532
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	98.67780303955078%
Volume Distribution (VD):	0.774
Pgp-substrate:	3.5061371326446533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.264
CYP1A2-substrate:	0.246
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.895
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.596
CYP2D6-substrate:	0.347
CYP3A4-inhibitor:	0.555
CYP3A4-substrate:	0.309

ADMET: Excretion

Clearance (CL):	7.904
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.79
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.158
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.946
Carcinogencity:	0.32
Eye Corrosion:	0.003
Eye Irritation:	0.839
Respiratory Toxicity:	0.562

Download Data

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

Natural Product: NPC101991

Natural Product ID:	NPC101991
*Common Name:**	SCNZCLDHJJSZBK-ROLQACJLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SCNZCLDHJJSZBK-ROLQACJLSA-N
Standard InCHI:	InChI=1S/C39H34O8/c1-19(2)4-8-26-30(42)11-10-29(38(26)44)39-37-27(25-9-7-24(41)18-34(25)46-39)12-20(3)13-28(37)36-31(43)14-22(16-35(36)47-39)32-15-21-5-6-23(40)17-33(21)45-32/h4-7,9-11,13-18,27-28,37,40-44H,8,12H2,1-3H3/t27-,28-,37-,39+/m0/s1
SMILES:	CC(=CCc1c(ccc(c1O)[C@@]12[C@H]3[C@@H](CC(=C[C@H]3c3c(cc(cc3O2)c2cc3ccc(cc3o2)O)O)C)c2ccc(cc2O1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3288841
PubChem CID:	3086294
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[17396934]
NPO23793	Morus lhou	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[18608767]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544568]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23793	Morus lhou	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23793	Morus lhou	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23793	Morus lhou	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16194	Morus bombycis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	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
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1200.0	nM	PMID[470393]

☑ 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 NPC101991 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	442
0.1-0.2	1773
0.2-0.3	3683
0.3-0.4	9544
0.4-0.5	9285
0.5-0.6	3858
0.6-0.7	5862
0.7-0.8	5547
0.8-0.85	2292
0.85-0.9	396
0.9-0.95	6
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9879	High Similarity	NPC121888
0.9877	High Similarity	NPC24748
0.9877	High Similarity	NPC59491
0.9632	High Similarity	NPC253730
0.9632	High Similarity	NPC286230
0.9509	High Similarity	NPC169471
0.9329	High Similarity	NPC159508
0.908	High Similarity	NPC137100
0.9059	High Similarity	NPC73899
0.9059	High Similarity	NPC474276
0.9059	High Similarity	NPC17105
0.9059	High Similarity	NPC147363
0.9042	High Similarity	NPC473010
0.9036	High Similarity	NPC473012
0.9006	High Similarity	NPC300657
0.8988	High Similarity	NPC251336
0.8982	High Similarity	NPC473009
0.8976	High Similarity	NPC301256
0.8976	High Similarity	NPC312273
0.8963	High Similarity	NPC54830
0.8963	High Similarity	NPC56049
0.8916	High Similarity	NPC195136
0.8869	High Similarity	NPC38591
0.8864	High Similarity	NPC87583
0.8855	High Similarity	NPC51760
0.8855	High Similarity	NPC105584
0.8824	High Similarity	NPC292233
0.881	High Similarity	NPC15374
0.8802	High Similarity	NPC98023
0.8802	High Similarity	NPC226462
0.8802	High Similarity	NPC312993
0.8795	High Similarity	NPC96342
0.8795	High Similarity	NPC212967
0.8795	High Similarity	NPC246647
0.8795	High Similarity	NPC164110
0.8795	High Similarity	NPC1796
0.8788	High Similarity	NPC297531
0.8788	High Similarity	NPC213936
0.8779	High Similarity	NPC477529
0.8773	High Similarity	NPC78335
0.8773	High Similarity	NPC230713
0.8773	High Similarity	NPC167576
0.8772	High Similarity	NPC470207
0.8772	High Similarity	NPC470206
0.875	High Similarity	NPC273467
0.875	High Similarity	NPC189552
0.8743	High Similarity	NPC299149
0.8743	High Similarity	NPC153578
0.8743	High Similarity	NPC277710
0.8743	High Similarity	NPC15815
0.8743	High Similarity	NPC51247
0.8743	High Similarity	NPC114257
0.8743	High Similarity	NPC177650
0.8735	High Similarity	NPC180924
0.8735	High Similarity	NPC69531
0.8728	High Similarity	NPC168789
0.8727	High Similarity	NPC213608
0.8727	High Similarity	NPC472462
0.8727	High Similarity	NPC1477
0.8727	High Similarity	NPC235333
0.8727	High Similarity	NPC72370
0.8721	High Similarity	NPC8704
0.8721	High Similarity	NPC477571
0.8721	High Similarity	NPC477572
0.8721	High Similarity	NPC287884
0.8721	High Similarity	NPC477573
0.872	High Similarity	NPC170169
0.8712	High Similarity	NPC178202
0.8708	High Similarity	NPC73929
0.8708	High Similarity	NPC47905
0.8708	High Similarity	NPC139683
0.8698	High Similarity	NPC473011
0.8698	High Similarity	NPC477528
0.869	High Similarity	NPC121647
0.869	High Similarity	NPC472060
0.869	High Similarity	NPC42965
0.869	High Similarity	NPC186325
0.869	High Similarity	NPC470342
0.869	High Similarity	NPC472052
0.8686	High Similarity	NPC478000
0.8683	High Similarity	NPC257166
0.8683	High Similarity	NPC268360
0.8683	High Similarity	NPC65504
0.8683	High Similarity	NPC475184
0.8683	High Similarity	NPC287789
0.8683	High Similarity	NPC271741
0.8675	High Similarity	NPC134171
0.8675	High Similarity	NPC121649
0.8675	High Similarity	NPC248739
0.8675	High Similarity	NPC186227
0.8675	High Similarity	NPC150908
0.8675	High Similarity	NPC205026
0.8675	High Similarity	NPC14606
0.8675	High Similarity	NPC37253
0.8675	High Similarity	NPC300668
0.8675	High Similarity	NPC159707
0.8675	High Similarity	NPC100049
0.8675	High Similarity	NPC158027
0.8675	High Similarity	NPC79375
0.8675	High Similarity	NPC215203
0.8675	High Similarity	NPC265624
0.8675	High Similarity	NPC52611
0.8675	High Similarity	NPC148938
0.8667	High Similarity	NPC5871
0.8667	High Similarity	NPC142308
0.8663	High Similarity	NPC53252
0.8652	High Similarity	NPC475220
0.8652	High Similarity	NPC229817
0.8652	High Similarity	NPC475352
0.8652	High Similarity	NPC473686
0.8652	High Similarity	NPC304322
0.8652	High Similarity	NPC221140
0.8647	High Similarity	NPC155640
0.8644	High Similarity	NPC473717
0.8644	High Similarity	NPC473631
0.8644	High Similarity	NPC475662
0.8644	High Similarity	NPC293227
0.8639	High Similarity	NPC175513
0.8639	High Similarity	NPC18380
0.8631	High Similarity	NPC244750
0.8631	High Similarity	NPC18699
0.8631	High Similarity	NPC40583
0.8631	High Similarity	NPC474373
0.8631	High Similarity	NPC55443
0.8631	High Similarity	NPC472877
0.8629	High Similarity	NPC475246
0.8629	High Similarity	NPC46958
0.8623	High Similarity	NPC198489
0.8623	High Similarity	NPC32867
0.8623	High Similarity	NPC309648
0.8623	High Similarity	NPC61112
0.8614	High Similarity	NPC72425
0.8614	High Similarity	NPC121568
0.8614	High Similarity	NPC303485
0.8614	High Similarity	NPC71061
0.8614	High Similarity	NPC194593
0.8614	High Similarity	NPC290830
0.8606	High Similarity	NPC222713
0.8606	High Similarity	NPC149085
0.8606	High Similarity	NPC111112
0.8606	High Similarity	NPC67322
0.8606	High Similarity	NPC193976
0.8606	High Similarity	NPC23668
0.8606	High Similarity	NPC138299
0.8598	High Similarity	NPC226644
0.8598	High Similarity	NPC37226
0.8596	High Similarity	NPC474591
0.8596	High Similarity	NPC469664
0.8588	High Similarity	NPC477860
0.8588	High Similarity	NPC477239
0.8588	High Similarity	NPC310603
0.8588	High Similarity	NPC3448
0.8588	High Similarity	NPC475161
0.858	High Similarity	NPC292863
0.858	High Similarity	NPC5671
0.858	High Similarity	NPC184326
0.858	High Similarity	NPC115432
0.858	High Similarity	NPC260296
0.8571	High Similarity	NPC322459
0.8571	High Similarity	NPC324358
0.8571	High Similarity	NPC3718
0.8571	High Similarity	NPC323627
0.8571	High Similarity	NPC318527
0.8571	High Similarity	NPC208258
0.8564	High Similarity	NPC264302
0.8563	High Similarity	NPC226656
0.8563	High Similarity	NPC182555
0.8563	High Similarity	NPC99199
0.8563	High Similarity	NPC477836
0.8563	High Similarity	NPC66508
0.8563	High Similarity	NPC198490
0.8563	High Similarity	NPC201227
0.8563	High Similarity	NPC258474
0.8563	High Similarity	NPC275575
0.8563	High Similarity	NPC254351
0.8563	High Similarity	NPC66441
0.8563	High Similarity	NPC478002
0.8554	High Similarity	NPC207624
0.8547	High Similarity	NPC477835
0.8547	High Similarity	NPC224851
0.8539	High Similarity	NPC132111
0.8539	High Similarity	NPC321916
0.8537	High Similarity	NPC135325
0.8537	High Similarity	NPC152233
0.8529	High Similarity	NPC137232
0.8529	High Similarity	NPC472261
0.8528	High Similarity	NPC110882
0.8528	High Similarity	NPC210826
0.8528	High Similarity	NPC271944
0.8528	High Similarity	NPC85393
0.8523	High Similarity	NPC472661
0.8523	High Similarity	NPC289876
0.8523	High Similarity	NPC475233
0.8521	High Similarity	NPC295090
0.8521	High Similarity	NPC195167
0.8521	High Similarity	NPC324736
0.8521	High Similarity	NPC226287
0.8521	High Similarity	NPC90497
0.8514	High Similarity	NPC213052
0.8514	High Similarity	NPC470335

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 NPC101991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	981
0.2-0.3	1601
0.3-0.4	2675
0.4-0.5	2033
0.5-0.6	974
0.6-0.7	308
0.7-0.8	159
0.8-0.85	25
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD6959	Discontinued
0.8514	High Similarity	NPD6559	Discontinued
0.8488	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3749	Approved
0.8452	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD8312	Approved
0.8315	Intermediate Similarity	NPD8313	Approved
0.8294	Intermediate Similarity	NPD7768	Phase 2
0.8284	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD7473	Discontinued
0.8166	Intermediate Similarity	NPD7411	Suspended
0.809	Intermediate Similarity	NPD7074	Phase 3
0.8087	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7390	Discontinued
0.8057	Intermediate Similarity	NPD6232	Discontinued
0.8046	Intermediate Similarity	NPD5494	Approved
0.8035	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7054	Approved
0.8024	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7472	Approved
0.7978	Intermediate Similarity	NPD3818	Discontinued
0.7966	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6166	Phase 2
0.7965	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7808	Phase 3
0.7931	Intermediate Similarity	NPD7075	Discontinued
0.7901	Intermediate Similarity	NPD7251	Discontinued
0.7895	Intermediate Similarity	NPD4380	Phase 2
0.7846	Intermediate Similarity	NPD8151	Discontinued
0.7845	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6797	Phase 2
0.7836	Intermediate Similarity	NPD3226	Approved
0.7833	Intermediate Similarity	NPD5844	Phase 1
0.7831	Intermediate Similarity	NPD2800	Approved
0.7818	Intermediate Similarity	NPD2344	Approved
0.7811	Intermediate Similarity	NPD2533	Approved
0.7811	Intermediate Similarity	NPD2532	Approved
0.7811	Intermediate Similarity	NPD2534	Approved
0.7771	Intermediate Similarity	NPD1549	Phase 2
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD1243	Approved
0.7719	Intermediate Similarity	NPD920	Approved
0.7711	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1934	Approved
0.7683	Intermediate Similarity	NPD1607	Approved
0.768	Intermediate Similarity	NPD7698	Approved
0.768	Intermediate Similarity	NPD7696	Phase 3
0.768	Intermediate Similarity	NPD7697	Approved
0.7679	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3750	Approved
0.767	Intermediate Similarity	NPD3882	Suspended
0.7657	Intermediate Similarity	NPD2801	Approved
0.7657	Intermediate Similarity	NPD8455	Phase 2
0.7647	Intermediate Similarity	NPD1511	Approved
0.7641	Intermediate Similarity	NPD7870	Phase 2
0.7641	Intermediate Similarity	NPD7871	Phase 2
0.7633	Intermediate Similarity	NPD2309	Approved
0.763	Intermediate Similarity	NPD7458	Discontinued
0.7611	Intermediate Similarity	NPD3926	Phase 2
0.7605	Intermediate Similarity	NPD2346	Discontinued
0.7602	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1510	Phase 2
0.7588	Intermediate Similarity	NPD7783	Phase 2
0.7588	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1240	Approved
0.7558	Intermediate Similarity	NPD1512	Approved
0.7557	Intermediate Similarity	NPD1465	Phase 2
0.7545	Intermediate Similarity	NPD5406	Approved
0.7545	Intermediate Similarity	NPD5405	Approved
0.7545	Intermediate Similarity	NPD2796	Approved
0.7545	Intermediate Similarity	NPD6100	Approved
0.7545	Intermediate Similarity	NPD6099	Approved
0.7545	Intermediate Similarity	NPD5408	Approved
0.7545	Intermediate Similarity	NPD5404	Approved
0.754	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6779	Approved
0.7526	Intermediate Similarity	NPD6778	Approved
0.7526	Intermediate Similarity	NPD6782	Approved
0.7526	Intermediate Similarity	NPD6776	Approved
0.7526	Intermediate Similarity	NPD6777	Approved
0.7526	Intermediate Similarity	NPD6780	Approved
0.7526	Intermediate Similarity	NPD6781	Approved
0.7525	Intermediate Similarity	NPD7701	Phase 2
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6599	Discontinued
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7486	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7459	Intermediate Similarity	NPD7229	Phase 3
0.7456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2935	Discontinued
0.7429	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7699	Phase 2
0.7423	Intermediate Similarity	NPD7700	Phase 2
0.7416	Intermediate Similarity	NPD3817	Phase 2
0.7413	Intermediate Similarity	NPD7801	Approved
0.7407	Intermediate Similarity	NPD8150	Discontinued
0.7407	Intermediate Similarity	NPD8434	Phase 2
0.7403	Intermediate Similarity	NPD1247	Approved
0.7391	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD919	Approved
0.7381	Intermediate Similarity	NPD3748	Approved
0.7374	Intermediate Similarity	NPD8320	Phase 1
0.7374	Intermediate Similarity	NPD8319	Approved
0.7368	Intermediate Similarity	NPD7003	Approved
0.7365	Intermediate Similarity	NPD6651	Approved
0.7363	Intermediate Similarity	NPD5711	Approved
0.7363	Intermediate Similarity	NPD7874	Approved
0.7363	Intermediate Similarity	NPD5710	Approved
0.7363	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3787	Discontinued
0.736	Intermediate Similarity	NPD6823	Phase 2
0.7341	Intermediate Similarity	NPD6799	Approved
0.7337	Intermediate Similarity	NPD1551	Phase 2
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5402	Approved
0.7308	Intermediate Similarity	NPD7199	Phase 2
0.7303	Intermediate Similarity	NPD37	Approved
0.7294	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6234	Discontinued
0.7287	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD5953	Discontinued
0.7268	Intermediate Similarity	NPD6535	Approved
0.7268	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7286	Phase 2
0.7229	Intermediate Similarity	NPD2313	Discontinued
0.7228	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4908	Phase 1
0.7204	Intermediate Similarity	NPD7177	Discontinued
0.72	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2798	Approved
0.7169	Intermediate Similarity	NPD4625	Phase 3
0.7167	Intermediate Similarity	NPD5761	Phase 2
0.7167	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2296	Approved
0.7126	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5403	Approved
0.7107	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1471	Phase 3
0.7069	Intermediate Similarity	NPD4628	Phase 3
0.7053	Intermediate Similarity	NPD7685	Pre-registration
0.7044	Intermediate Similarity	NPD7584	Approved
0.7041	Intermediate Similarity	NPD6213	Phase 3
0.7041	Intermediate Similarity	NPD943	Approved
0.7041	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6212	Phase 3
0.7024	Intermediate Similarity	NPD3764	Approved
0.7014	Intermediate Similarity	NPD8366	Approved
0.7012	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD5401	Approved
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7680	Approved
0.6966	Remote Similarity	NPD6273	Approved
0.6961	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8059	Phase 3
0.693	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1203	Approved
0.6928	Remote Similarity	NPD1470	Approved
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8067	Phase 3
0.6905	Remote Similarity	NPD6832	Phase 2
0.6884	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4361	Phase 2
0.6884	Remote Similarity	NPD8491	Approved
0.6879	Remote Similarity	NPD4308	Phase 3
0.6866	Remote Similarity	NPD8285	Discontinued
0.6848	Remote Similarity	NPD1608	Approved
0.6848	Remote Similarity	NPD4288	Approved
0.6845	Remote Similarity	NPD8127	Discontinued
0.6831	Remote Similarity	NPD6279	Approved
0.6831	Remote Similarity	NPD6280	Approved
0.6828	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2797	Approved
0.6824	Remote Similarity	NPD411	Approved
0.6821	Remote Similarity	NPD7097	Phase 1

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