NPASS Compound

Structure

CID269492 OpenBabel06191716072D 33 35 0 0 1 0 0 0 0 0999 V2000 4.1000 1.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2806 2.8391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8202 1.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1141 2.7127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6395 1.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8195 -0.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4600 -0.4732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0396 -3.2249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4597 0.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2205 2.7135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1673 2.7131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6396 -0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 1.8935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2802 1.8923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 0.9466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4601 1.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8202 1.4199 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2526 3.5336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6398 0.9472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8201 -0.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 -0.9465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6403 1.8930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8197 1.4204 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8198 0.4731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6400 0.0001 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 -1.1994 3.5340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2211 4.3534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4596 1.4208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8202 -1.4200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9198 -1.1696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4599 0.4735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3064 -2.3168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 6 24 1 0 0 0 0 8 33 1 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 15 23 1 0 0 0 0 15 26 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 1 0 0 0 17 24 1 0 0 0 0 18 27 2 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 20 30 2 0 0 0 0 21 31 2 0 0 0 0 21 33 1 0 0 0 0 22 4 1 1 0 0 0 23 5 1 1 0 0 0 24 26 1 6 0 0 0 25 7 1 6 0 0 0 25 32 1 0 0 0 0 26 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.23
Volume:	475.659
LogP:	2.926
LogD:	2.133
LogS:	-4.366
# Rotatable Bonds:	6
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	5.871
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.622
MDCK Permeability:	2.6684292606660165e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.287
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.883
Plasma Protein Binding (PPB):	73.28968048095703%
Volume Distribution (VD):	0.274
Pgp-substrate:	23.808189392089844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.105
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.561
CYP3A4-substrate:	0.942

ADMET: Excretion

Clearance (CL):	1.729
Half-life (T1/2):	0.359

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.702
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.161
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.144
Skin Sensitization:	0.267
Carcinogencity:	0.787
Eye Corrosion:	0.942
Eye Irritation:	0.125
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC269492

Natural Product ID:	NPC269492
*Common Name:**	Berkeleyone C
IUPAC Name:	n.a.
Synonyms:	Berkeleyone C
Standard InCHIKey:	HBZLILHFZMWEGE-QFRJCEMRSA-N
Standard InCHI:	InChI=1S/C26H34O7/c1-14(2)16-9-12-24(6)17(22(16,4)11-10-18(27)28)13-23(5)15(3)26(24,21(31)33-8)20(30)25(7,32)19(23)29/h9,17,32H,1,3,10-13H2,2,4-8H3,(H,27,28)/t17-,22+,23+,24-,25-,26-/m0/s1
SMILES:	COC(=O)[C@@]12C(=O)[C@@](C)(O)C(=O)[C@](C1=C)(C)C[C@@H]1[C@]2(C)CC=C([C@@]1(C)CCC(=O)O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911630
PubChem CID:	57401571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids 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
NPO10881	Gyrophyllum sibogae	Species	Pennatulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270580]
NPO3909	Leucas aspera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872130]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	Berkeley Pit Lake, Butte, Montana	n.a.	PMID[18330993]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22295871]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3909	Leucas aspera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9306	Globularia nudicaulis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15438	Stemona parviflora	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10881	Gyrophyllum sibogae	Species	Pennatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3221	Schkuhria anthemoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3909	Leucas aspera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO263	Clibadium microcephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17828	Talaromyces ruber	Species	Trichocomaceae	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	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT277	Individual Protein	Caspase-1	Homo sapiens	Inhibition	=	0.0	%	PMID[558067]
NPT5270	Individual Protein	Interleukin-1 beta	Homo sapiens	IC50	=	37800.0	nM	PMID[558067]

☑ 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 NPC269492 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	207
0.1-0.2	1173
0.2-0.3	4549
0.3-0.4	10470
0.4-0.5	13011
0.5-0.6	7066
0.6-0.7	5009
0.7-0.8	1180
0.8-0.85	29
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8958	High Similarity	NPC323441
0.8878	High Similarity	NPC325769
0.8804	High Similarity	NPC263977
0.871	High Similarity	NPC327515
0.8438	Intermediate Similarity	NPC777
0.8351	Intermediate Similarity	NPC223169
0.8333	Intermediate Similarity	NPC148964
0.8229	Intermediate Similarity	NPC263780
0.8202	Intermediate Similarity	NPC28319
0.8163	Intermediate Similarity	NPC157113
0.8163	Intermediate Similarity	NPC62516
0.8137	Intermediate Similarity	NPC213366
0.8137	Intermediate Similarity	NPC284865
0.8125	Intermediate Similarity	NPC470036
0.8125	Intermediate Similarity	NPC174167
0.8113	Intermediate Similarity	NPC193948
0.8105	Intermediate Similarity	NPC474700
0.81	Intermediate Similarity	NPC46761
0.809	Intermediate Similarity	NPC321514
0.8065	Intermediate Similarity	NPC474680
0.8065	Intermediate Similarity	NPC76333
0.8061	Intermediate Similarity	NPC147232
0.8058	Intermediate Similarity	NPC85529
0.8058	Intermediate Similarity	NPC292588
0.8058	Intermediate Similarity	NPC32006
0.8043	Intermediate Similarity	NPC102197
0.8022	Intermediate Similarity	NPC142244
0.8021	Intermediate Similarity	NPC476437
0.8021	Intermediate Similarity	NPC476369
0.8	Intermediate Similarity	NPC1753
0.8	Intermediate Similarity	NPC474511
0.798	Intermediate Similarity	NPC132824
0.7979	Intermediate Similarity	NPC229717
0.7979	Intermediate Similarity	NPC262085
0.7979	Intermediate Similarity	NPC73038
0.7938	Intermediate Similarity	NPC38754
0.7921	Intermediate Similarity	NPC474802
0.7917	Intermediate Similarity	NPC474570
0.7917	Intermediate Similarity	NPC118011
0.7917	Intermediate Similarity	NPC112454
0.7917	Intermediate Similarity	NPC36668
0.7912	Intermediate Similarity	NPC37038
0.7912	Intermediate Similarity	NPC104545
0.79	Intermediate Similarity	NPC473161
0.79	Intermediate Similarity	NPC170131
0.79	Intermediate Similarity	NPC187933
0.7895	Intermediate Similarity	NPC96496
0.7895	Intermediate Similarity	NPC476409
0.7895	Intermediate Similarity	NPC158141
0.7895	Intermediate Similarity	NPC477926
0.7895	Intermediate Similarity	NPC173089
0.7879	Intermediate Similarity	NPC263347
0.7864	Intermediate Similarity	NPC275583
0.7864	Intermediate Similarity	NPC90177
0.7857	Intermediate Similarity	NPC118519
0.7857	Intermediate Similarity	NPC158059
0.7857	Intermediate Similarity	NPC118490
0.7857	Intermediate Similarity	NPC202728
0.7857	Intermediate Similarity	NPC476416
0.7849	Intermediate Similarity	NPC105803
0.7849	Intermediate Similarity	NPC477373
0.7849	Intermediate Similarity	NPC473592
0.7849	Intermediate Similarity	NPC70834
0.7843	Intermediate Similarity	NPC118964
0.7843	Intermediate Similarity	NPC472702
0.7843	Intermediate Similarity	NPC472685
0.7835	Intermediate Similarity	NPC46441
0.7835	Intermediate Similarity	NPC193750
0.7826	Intermediate Similarity	NPC474955
0.7826	Intermediate Similarity	NPC189237
0.7826	Intermediate Similarity	NPC221647
0.7826	Intermediate Similarity	NPC278459
0.7826	Intermediate Similarity	NPC327002
0.7822	Intermediate Similarity	NPC174663
0.7812	Intermediate Similarity	NPC72397
0.7812	Intermediate Similarity	NPC474474
0.7802	Intermediate Similarity	NPC231431
0.7802	Intermediate Similarity	NPC199595
0.78	Intermediate Similarity	NPC327179
0.78	Intermediate Similarity	NPC469528
0.78	Intermediate Similarity	NPC469369
0.7789	Intermediate Similarity	NPC324063
0.7778	Intermediate Similarity	NPC476415
0.7778	Intermediate Similarity	NPC114159
0.7778	Intermediate Similarity	NPC49670
0.7778	Intermediate Similarity	NPC6818
0.7778	Intermediate Similarity	NPC191412
0.7778	Intermediate Similarity	NPC474529
0.7766	Intermediate Similarity	NPC156981
0.7755	Intermediate Similarity	NPC471588
0.7755	Intermediate Similarity	NPC154101
0.7755	Intermediate Similarity	NPC105189
0.7755	Intermediate Similarity	NPC230064
0.7755	Intermediate Similarity	NPC474525
0.7755	Intermediate Similarity	NPC187722
0.7755	Intermediate Similarity	NPC6255
0.7755	Intermediate Similarity	NPC36491
0.7745	Intermediate Similarity	NPC35239
0.7742	Intermediate Similarity	NPC69101
0.7742	Intermediate Similarity	NPC302661
0.7742	Intermediate Similarity	NPC238991
0.7742	Intermediate Similarity	NPC15910
0.7742	Intermediate Similarity	NPC251779
0.7736	Intermediate Similarity	NPC469508
0.7736	Intermediate Similarity	NPC168883
0.7732	Intermediate Similarity	NPC472688
0.7732	Intermediate Similarity	NPC65615
0.7732	Intermediate Similarity	NPC472676
0.7732	Intermediate Similarity	NPC477973
0.7732	Intermediate Similarity	NPC68148
0.7723	Intermediate Similarity	NPC259788
0.7723	Intermediate Similarity	NPC43747
0.7723	Intermediate Similarity	NPC21728
0.7723	Intermediate Similarity	NPC89225
0.7723	Intermediate Similarity	NPC255589
0.7717	Intermediate Similarity	NPC477057
0.7708	Intermediate Similarity	NPC181327
0.7706	Intermediate Similarity	NPC159333
0.7706	Intermediate Similarity	NPC326264
0.7706	Intermediate Similarity	NPC474271
0.77	Intermediate Similarity	NPC31021
0.77	Intermediate Similarity	NPC469599
0.77	Intermediate Similarity	NPC139459
0.77	Intermediate Similarity	NPC195715
0.77	Intermediate Similarity	NPC53565
0.7692	Intermediate Similarity	NPC179208
0.7692	Intermediate Similarity	NPC474207
0.7692	Intermediate Similarity	NPC260385
0.7692	Intermediate Similarity	NPC280654
0.7692	Intermediate Similarity	NPC474330
0.7692	Intermediate Similarity	NPC320294
0.7692	Intermediate Similarity	NPC110094
0.7685	Intermediate Similarity	NPC34315
0.7684	Intermediate Similarity	NPC6185
0.7684	Intermediate Similarity	NPC241512
0.7677	Intermediate Similarity	NPC170220
0.7677	Intermediate Similarity	NPC107674
0.7677	Intermediate Similarity	NPC477435
0.7677	Intermediate Similarity	NPC66429
0.7677	Intermediate Similarity	NPC141497
0.7677	Intermediate Similarity	NPC152897
0.7677	Intermediate Similarity	NPC474807
0.7677	Intermediate Similarity	NPC477436
0.7677	Intermediate Similarity	NPC229281
0.7677	Intermediate Similarity	NPC131840
0.767	Intermediate Similarity	NPC475867
0.767	Intermediate Similarity	NPC270155
0.7667	Intermediate Similarity	NPC899
0.7667	Intermediate Similarity	NPC69143
0.7667	Intermediate Similarity	NPC309399
0.7664	Intermediate Similarity	NPC300026
0.7664	Intermediate Similarity	NPC220705
0.7664	Intermediate Similarity	NPC23497
0.766	Intermediate Similarity	NPC69279
0.766	Intermediate Similarity	NPC83569
0.766	Intermediate Similarity	NPC312480
0.766	Intermediate Similarity	NPC200752
0.766	Intermediate Similarity	NPC476100
0.7653	Intermediate Similarity	NPC477872
0.7653	Intermediate Similarity	NPC18872
0.7653	Intermediate Similarity	NPC7260
0.7653	Intermediate Similarity	NPC290614
0.7653	Intermediate Similarity	NPC291028
0.7653	Intermediate Similarity	NPC273621
0.7653	Intermediate Similarity	NPC210037
0.7653	Intermediate Similarity	NPC474728
0.7653	Intermediate Similarity	NPC227467
0.7653	Intermediate Similarity	NPC120968
0.7647	Intermediate Similarity	NPC153776
0.7647	Intermediate Similarity	NPC472729
0.7647	Intermediate Similarity	NPC29765
0.7647	Intermediate Similarity	NPC164349
0.7647	Intermediate Similarity	NPC271614
0.7647	Intermediate Similarity	NPC177680
0.7647	Intermediate Similarity	NPC111214
0.7647	Intermediate Similarity	NPC472730
0.7634	Intermediate Similarity	NPC472684
0.7634	Intermediate Similarity	NPC476101
0.7634	Intermediate Similarity	NPC267691
0.7634	Intermediate Similarity	NPC471898
0.7634	Intermediate Similarity	NPC274050
0.7634	Intermediate Similarity	NPC121984
0.7634	Intermediate Similarity	NPC44963
0.7634	Intermediate Similarity	NPC162632
0.7634	Intermediate Similarity	NPC147066
0.7634	Intermediate Similarity	NPC263272
0.7629	Intermediate Similarity	NPC48107
0.7624	Intermediate Similarity	NPC235053
0.7624	Intermediate Similarity	NPC98874
0.7624	Intermediate Similarity	NPC472806
0.7624	Intermediate Similarity	NPC155676
0.7624	Intermediate Similarity	NPC207922
0.7624	Intermediate Similarity	NPC167193
0.7624	Intermediate Similarity	NPC116457
0.7624	Intermediate Similarity	NPC158371
0.7624	Intermediate Similarity	NPC471153
0.7624	Intermediate Similarity	NPC259733
0.7619	Intermediate Similarity	NPC475036
0.7619	Intermediate Similarity	NPC13385
0.7609	Intermediate Similarity	NPC474113

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 NPC269492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1463
0.2-0.3	3720
0.3-0.4	2436
0.4-0.5	868
0.5-0.6	235
0.6-0.7	167
0.7-0.8	68
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
0.7917	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6399	Phase 3
0.7822	Intermediate Similarity	NPD5696	Approved
0.7755	Intermediate Similarity	NPD6411	Approved
0.7576	Intermediate Similarity	NPD5281	Approved
0.7576	Intermediate Similarity	NPD5284	Approved
0.7551	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6101	Approved
0.7549	Intermediate Similarity	NPD7902	Approved
0.7549	Intermediate Similarity	NPD6083	Phase 2
0.7549	Intermediate Similarity	NPD6084	Phase 2
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.7527	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.7449	Intermediate Similarity	NPD5737	Approved
0.7449	Intermediate Similarity	NPD6672	Approved
0.7426	Intermediate Similarity	NPD7748	Approved
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6098	Approved
0.7407	Intermediate Similarity	NPD6899	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.7407	Intermediate Similarity	NPD6881	Approved
0.74	Intermediate Similarity	NPD7515	Phase 2
0.74	Intermediate Similarity	NPD6050	Approved
0.7374	Intermediate Similarity	NPD6673	Approved
0.7374	Intermediate Similarity	NPD6904	Approved
0.7374	Intermediate Similarity	NPD6080	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7353	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5695	Phase 3
0.7353	Intermediate Similarity	NPD5210	Approved
0.732	Intermediate Similarity	NPD5329	Approved
0.7315	Intermediate Similarity	NPD5701	Approved
0.7315	Intermediate Similarity	NPD5697	Approved
0.73	Intermediate Similarity	NPD5692	Phase 3
0.7273	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD7102	Approved
0.7273	Intermediate Similarity	NPD6883	Approved
0.7255	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7900	Approved
0.7248	Intermediate Similarity	NPD6011	Approved
0.7245	Intermediate Similarity	NPD5280	Approved
0.7245	Intermediate Similarity	NPD4694	Approved
0.7228	Intermediate Similarity	NPD5694	Approved
0.7216	Intermediate Similarity	NPD4786	Approved
0.7216	Intermediate Similarity	NPD4197	Approved
0.7212	Intermediate Similarity	NPD4755	Approved
0.7207	Intermediate Similarity	NPD8130	Phase 1
0.7207	Intermediate Similarity	NPD6847	Approved
0.7207	Intermediate Similarity	NPD6617	Approved
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6869	Approved
0.72	Intermediate Similarity	NPD4753	Phase 2
0.7188	Intermediate Similarity	NPD3667	Approved
0.7184	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6013	Approved
0.7182	Intermediate Similarity	NPD6012	Approved
0.7182	Intermediate Similarity	NPD6014	Approved
0.7172	Intermediate Similarity	NPD3573	Approved
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7115	Intermediate Similarity	NPD7614	Phase 1
0.7115	Intermediate Similarity	NPD4697	Phase 3
0.7075	Intermediate Similarity	NPD4700	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD3618	Phase 1
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7071	Intermediate Similarity	NPD5279	Phase 3
0.7071	Intermediate Similarity	NPD7521	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.703	Intermediate Similarity	NPD5328	Approved
0.701	Intermediate Similarity	NPD4223	Phase 3
0.701	Intermediate Similarity	NPD4221	Approved
0.7009	Intermediate Similarity	NPD5223	Approved
0.6961	Remote Similarity	NPD5207	Approved
0.6952	Remote Similarity	NPD7732	Phase 3
0.6952	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5222	Approved
0.6952	Remote Similarity	NPD5221	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6944	Remote Similarity	NPD5224	Approved
0.6937	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6903	Approved
0.693	Remote Similarity	NPD4632	Approved
0.6909	Remote Similarity	NPD6008	Approved
0.69	Remote Similarity	NPD5690	Phase 2
0.6897	Remote Similarity	NPD7115	Discovery
0.6893	Remote Similarity	NPD8034	Phase 2
0.6893	Remote Similarity	NPD6079	Approved
0.6893	Remote Similarity	NPD8035	Phase 2
0.6887	Remote Similarity	NPD5173	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD4754	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6869	Remote Similarity	NPD3665	Phase 1
0.6869	Remote Similarity	NPD3133	Approved
0.6869	Remote Similarity	NPD3666	Approved
0.6869	Remote Similarity	NPD3668	Phase 3
0.6864	Remote Similarity	NPD6319	Approved
0.6857	Remote Similarity	NPD5654	Approved
0.6847	Remote Similarity	NPD6614	Approved
0.6838	Remote Similarity	NPD6335	Approved
0.6833	Remote Similarity	NPD8328	Phase 3
0.6827	Remote Similarity	NPD4202	Approved
0.6818	Remote Similarity	NPD5141	Approved
0.6814	Remote Similarity	NPD4634	Approved
0.681	Remote Similarity	NPD6274	Approved
0.6789	Remote Similarity	NPD5091	Approved
0.678	Remote Similarity	NPD7101	Approved
0.678	Remote Similarity	NPD7100	Approved
0.6777	Remote Similarity	NPD7492	Approved
0.6765	Remote Similarity	NPD5208	Approved
0.6762	Remote Similarity	NPD6001	Approved
0.6757	Remote Similarity	NPD4768	Approved
0.6757	Remote Similarity	NPD4767	Approved
0.6752	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6009	Approved
0.6752	Remote Similarity	NPD6317	Approved
0.6735	Remote Similarity	NPD5369	Approved
0.6733	Remote Similarity	NPD4623	Approved
0.6733	Remote Similarity	NPD4693	Phase 3
0.6733	Remote Similarity	NPD4689	Approved
0.6733	Remote Similarity	NPD4688	Approved
0.6733	Remote Similarity	NPD4138	Approved
0.6733	Remote Similarity	NPD4690	Approved
0.6733	Remote Similarity	NPD5205	Approved
0.6733	Remote Similarity	NPD4519	Discontinued
0.6729	Remote Similarity	NPD5959	Approved
0.6723	Remote Similarity	NPD6054	Approved
0.6723	Remote Similarity	NPD6059	Approved
0.6721	Remote Similarity	NPD6616	Approved
0.6695	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5133	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD5128	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6634	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7736	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.6604	Remote Similarity	NPD5282	Discontinued
0.6571	Remote Similarity	NPD7637	Suspended
0.6557	Remote Similarity	NPD7604	Phase 2
0.6529	Remote Similarity	NPD5983	Phase 2
0.6529	Remote Similarity	NPD6015	Approved
0.6529	Remote Similarity	NPD6016	Approved
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5135	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5169	Approved
0.6522	Remote Similarity	NPD5248	Approved
0.6522	Remote Similarity	NPD5250	Approved
0.6522	Remote Similarity	NPD5251	Approved
0.6522	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4225	Approved
0.6514	Remote Similarity	NPD7638	Approved
0.65	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6081	Approved
0.6476	Remote Similarity	NPD4096	Approved
0.6475	Remote Similarity	NPD5988	Approved
0.6471	Remote Similarity	NPD1696	Phase 3
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD5127	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6465	Remote Similarity	NPD7525	Registered
0.6457	Remote Similarity	NPD7260	Phase 2
0.6455	Remote Similarity	NPD7640	Approved
0.6455	Remote Similarity	NPD7639	Approved
0.6452	Remote Similarity	NPD6336	Discontinued
0.6442	Remote Similarity	NPD4518	Approved
0.6436	Remote Similarity	NPD4788	Approved
0.6435	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6052	Approved
0.6408	Remote Similarity	NPD5786	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