NPASS Compound

Structure

NPC474328 OpenBabel07101718222D 31 35 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 3 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 2 0 0 0 0 7 18 2 0 0 0 0 8 9 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 14 2 1 1 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 24 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 6 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 28 2 0 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 29 1 1 0 0 0 24 30 1 0 0 0 0 25 31 2 0 0 0 0 26 4 1 1 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.23
Volume:	449.471
LogP:	4.675
LogD:	2.2
LogS:	-3.135
# Rotatable Bonds:	0
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.563
Synthetic Accessibility Score:	5.326
Fsp3:	0.519
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007
MDCK Permeability:	1.2360750588413794e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	98.07434844970703%
Volume Distribution (VD):	1.278
Pgp-substrate:	2.7250113487243652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.221
CYP1A2-substrate:	0.693
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.309
CYP2C9-substrate:	0.747
CYP2D6-inhibitor:	0.241
CYP2D6-substrate:	0.306
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.709

ADMET: Excretion

Clearance (CL):	3.643
Half-life (T1/2):	0.681

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.197
AMES Toxicity:	0.14
Rat Oral Acute Toxicity:	0.613
Maximum Recommended Daily Dose:	0.848
Skin Sensitization:	0.927
Carcinogencity:	0.445
Eye Corrosion:	0.003
Eye Irritation:	0.09
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC474328

Natural Product ID:	NPC474328
*Common Name:**	Balaenonol
IUPAC Name:	(6aS,10R,11R,12aR,14aS)-3,10-dihydroxy-4,6a,7,11,14a-pentamethyl-8,8a,10,11,12,12a,13,14-octahydropicene-2,9-dione
Synonyms:	Balaenonol
Standard InCHIKey:	ZNWQKMXMQWNIDO-XYTWUQDISA-N
Standard InCHI:	InChI=1S/C27H32O4/c1-13-10-17-19(11-14(2)23(29)25(17)31)27(5)9-8-26(4)18(22(13)27)7-6-16-15(3)24(30)21(28)12-20(16)26/h6-7,12,14,17,19,23,29-30H,8-11H2,1-5H3/t14-,17?,19-,23-,26-,27+/m1/s1
SMILES:	O[C@@H]1[C@H](C)C[C@@H]2C(C1=O)CC(=C1[C@@]2(C)CC[C@@]2(C1=CC=C1C2=CC(=O)C(=C1C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465320
PubChem CID:	44567178
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids

*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
NPO26894	Kokoona zeylanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678653]
NPO26894	Kokoona zeylanica	Species	Celastraceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	220.0	ug ml-1	PMID[565101]

☑ 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 NPC474328 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	201
0.1-0.2	1199
0.2-0.3	4437
0.3-0.4	11108
0.4-0.5	13212
0.5-0.6	6521
0.6-0.7	4551
0.7-0.8	1356
0.8-0.85	94
0.85-0.9	15
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9659	High Similarity	NPC211230
0.9333	High Similarity	NPC23170
0.9121	High Similarity	NPC474882
0.9101	High Similarity	NPC65615
0.9101	High Similarity	NPC68148
0.8989	High Similarity	NPC230387
0.8866	High Similarity	NPC213366
0.8696	High Similarity	NPC470036
0.8696	High Similarity	NPC174167
0.8681	High Similarity	NPC112454
0.8652	High Similarity	NPC32037
0.8636	High Similarity	NPC291999
0.8636	High Similarity	NPC309309
0.8621	High Similarity	NPC470034
0.8617	High Similarity	NPC280725
0.8602	High Similarity	NPC263780
0.8539	High Similarity	NPC53385
0.8523	High Similarity	NPC48362
0.8511	High Similarity	NPC245972
0.8511	High Similarity	NPC80365
0.8511	High Similarity	NPC160413
0.8511	High Similarity	NPC196485
0.8495	Intermediate Similarity	NPC4036
0.8495	Intermediate Similarity	NPC474525
0.8495	Intermediate Similarity	NPC233455
0.8495	Intermediate Similarity	NPC158030
0.8495	Intermediate Similarity	NPC145067
0.8495	Intermediate Similarity	NPC301244
0.8495	Intermediate Similarity	NPC65120
0.8462	Intermediate Similarity	NPC73064
0.8444	Intermediate Similarity	NPC133954
0.8427	Intermediate Similarity	NPC53733
0.8421	Intermediate Similarity	NPC777
0.8409	Intermediate Similarity	NPC121984
0.8409	Intermediate Similarity	NPC475863
0.8404	Intermediate Similarity	NPC214756
0.8404	Intermediate Similarity	NPC295643
0.8404	Intermediate Similarity	NPC272075
0.8387	Intermediate Similarity	NPC46441
0.837	Intermediate Similarity	NPC471722
0.837	Intermediate Similarity	NPC206060
0.837	Intermediate Similarity	NPC472802
0.8352	Intermediate Similarity	NPC74363
0.8352	Intermediate Similarity	NPC94666
0.8352	Intermediate Similarity	NPC158393
0.8352	Intermediate Similarity	NPC475862
0.8352	Intermediate Similarity	NPC56588
0.8352	Intermediate Similarity	NPC213412
0.8333	Intermediate Similarity	NPC157113
0.8333	Intermediate Similarity	NPC62516
0.8333	Intermediate Similarity	NPC88847
0.8333	Intermediate Similarity	NPC473158
0.8333	Intermediate Similarity	NPC180834
0.8315	Intermediate Similarity	NPC103486
0.8298	Intermediate Similarity	NPC185936
0.8298	Intermediate Similarity	NPC168027
0.8298	Intermediate Similarity	NPC99380
0.8295	Intermediate Similarity	NPC2482
0.8295	Intermediate Similarity	NPC287063
0.828	Intermediate Similarity	NPC274330
0.828	Intermediate Similarity	NPC474686
0.828	Intermediate Similarity	NPC95246
0.828	Intermediate Similarity	NPC1015
0.828	Intermediate Similarity	NPC31985
0.828	Intermediate Similarity	NPC198664
0.828	Intermediate Similarity	NPC161751
0.828	Intermediate Similarity	NPC474245
0.828	Intermediate Similarity	NPC143232
0.828	Intermediate Similarity	NPC474972
0.8261	Intermediate Similarity	NPC220930
0.8261	Intermediate Similarity	NPC475740
0.8261	Intermediate Similarity	NPC272039
0.8261	Intermediate Similarity	NPC141292
0.8261	Intermediate Similarity	NPC71507
0.8261	Intermediate Similarity	NPC470523
0.8247	Intermediate Similarity	NPC21728
0.8242	Intermediate Similarity	NPC33881
0.8242	Intermediate Similarity	NPC470574
0.8242	Intermediate Similarity	NPC197823
0.8229	Intermediate Similarity	NPC127063
0.8229	Intermediate Similarity	NPC147232
0.8229	Intermediate Similarity	NPC148523
0.8229	Intermediate Similarity	NPC139570
0.8211	Intermediate Similarity	NPC474806
0.8211	Intermediate Similarity	NPC12722
0.8211	Intermediate Similarity	NPC134826
0.8211	Intermediate Similarity	NPC133579
0.8202	Intermediate Similarity	NPC55869
0.8202	Intermediate Similarity	NPC225515
0.8191	Intermediate Similarity	NPC475823
0.8191	Intermediate Similarity	NPC126369
0.8191	Intermediate Similarity	NPC291028
0.8191	Intermediate Similarity	NPC85173
0.8191	Intermediate Similarity	NPC474209
0.8191	Intermediate Similarity	NPC470589
0.8191	Intermediate Similarity	NPC111110
0.8172	Intermediate Similarity	NPC470629
0.8172	Intermediate Similarity	NPC310752
0.8172	Intermediate Similarity	NPC290690
0.8172	Intermediate Similarity	NPC473242
0.8172	Intermediate Similarity	NPC182797
0.8172	Intermediate Similarity	NPC292491
0.8172	Intermediate Similarity	NPC17733
0.8172	Intermediate Similarity	NPC52169
0.8172	Intermediate Similarity	NPC474512
0.8172	Intermediate Similarity	NPC470524
0.8172	Intermediate Similarity	NPC181225
0.8163	Intermediate Similarity	NPC478056
0.8152	Intermediate Similarity	NPC51014
0.8152	Intermediate Similarity	NPC477579
0.8152	Intermediate Similarity	NPC145879
0.8152	Intermediate Similarity	NPC474778
0.8152	Intermediate Similarity	NPC474733
0.8152	Intermediate Similarity	NPC235341
0.8152	Intermediate Similarity	NPC72638
0.8152	Intermediate Similarity	NPC474732
0.8152	Intermediate Similarity	NPC72133
0.8152	Intermediate Similarity	NPC31564
0.8152	Intermediate Similarity	NPC95594
0.8144	Intermediate Similarity	NPC328162
0.8144	Intermediate Similarity	NPC9487
0.8144	Intermediate Similarity	NPC98874
0.8144	Intermediate Similarity	NPC305483
0.8144	Intermediate Similarity	NPC96859
0.8132	Intermediate Similarity	NPC171789
0.8125	Intermediate Similarity	NPC74751
0.8125	Intermediate Similarity	NPC474690
0.8111	Intermediate Similarity	NPC310989
0.8105	Intermediate Similarity	NPC272746
0.8105	Intermediate Similarity	NPC105189
0.8105	Intermediate Similarity	NPC187722
0.8105	Intermediate Similarity	NPC473167
0.8105	Intermediate Similarity	NPC235704
0.8105	Intermediate Similarity	NPC248913
0.8105	Intermediate Similarity	NPC38754
0.809	Intermediate Similarity	NPC108955
0.809	Intermediate Similarity	NPC18955
0.8085	Intermediate Similarity	NPC130520
0.8085	Intermediate Similarity	NPC270768
0.8085	Intermediate Similarity	NPC470588
0.8085	Intermediate Similarity	NPC290972
0.8085	Intermediate Similarity	NPC86319
0.8085	Intermediate Similarity	NPC61543
0.8085	Intermediate Similarity	NPC225585
0.8085	Intermediate Similarity	NPC293048
0.8085	Intermediate Similarity	NPC127689
0.8085	Intermediate Similarity	NPC25906
0.8085	Intermediate Similarity	NPC64872
0.8085	Intermediate Similarity	NPC119416
0.8085	Intermediate Similarity	NPC59263
0.8085	Intermediate Similarity	NPC234346
0.8085	Intermediate Similarity	NPC69627
0.8085	Intermediate Similarity	NPC121798
0.8085	Intermediate Similarity	NPC263393
0.8085	Intermediate Similarity	NPC275740
0.8068	Intermediate Similarity	NPC476808
0.8068	Intermediate Similarity	NPC30321
0.8068	Intermediate Similarity	NPC72507
0.8065	Intermediate Similarity	NPC130577
0.8065	Intermediate Similarity	NPC142415
0.8065	Intermediate Similarity	NPC68160
0.8065	Intermediate Similarity	NPC242468
0.8065	Intermediate Similarity	NPC51700
0.8065	Intermediate Similarity	NPC171203
0.8065	Intermediate Similarity	NPC88716
0.8065	Intermediate Similarity	NPC307426
0.8065	Intermediate Similarity	NPC98442
0.8065	Intermediate Similarity	NPC18064
0.8065	Intermediate Similarity	NPC102683
0.8065	Intermediate Similarity	NPC293564
0.8065	Intermediate Similarity	NPC58063
0.8046	Intermediate Similarity	NPC92080
0.8043	Intermediate Similarity	NPC132228
0.8043	Intermediate Similarity	NPC474680
0.8043	Intermediate Similarity	NPC6185
0.8043	Intermediate Similarity	NPC241512
0.8043	Intermediate Similarity	NPC8518
0.8043	Intermediate Similarity	NPC263997
0.8041	Intermediate Similarity	NPC32118
0.8041	Intermediate Similarity	NPC473170
0.8039	Intermediate Similarity	NPC478052
0.8022	Intermediate Similarity	NPC237795
0.8022	Intermediate Similarity	NPC82538
0.8022	Intermediate Similarity	NPC105803
0.8021	Intermediate Similarity	NPC229281
0.8021	Intermediate Similarity	NPC202728
0.8021	Intermediate Similarity	NPC158059
0.8021	Intermediate Similarity	NPC475255
0.8021	Intermediate Similarity	NPC118519
0.802	Intermediate Similarity	NPC179208
0.8	Intermediate Similarity	NPC210037
0.8	Intermediate Similarity	NPC48010
0.8	Intermediate Similarity	NPC129913
0.8	Intermediate Similarity	NPC3915
0.8	Intermediate Similarity	NPC290614
0.8	Intermediate Similarity	NPC273621
0.8	Intermediate Similarity	NPC227467
0.8	Intermediate Similarity	NPC113393
0.8	Intermediate Similarity	NPC474728
0.8	Intermediate Similarity	NPC193750

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 NPC474328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1509
0.2-0.3	3746
0.3-0.4	2507
0.4-0.5	777
0.5-0.6	164
0.6-0.7	171
0.7-0.8	89
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8681	High Similarity	NPD7285	Clinical (unspecified phase)
0.8495	Intermediate Similarity	NPD7515	Phase 2
0.8152	Intermediate Similarity	NPD5279	Phase 3
0.8152	Intermediate Similarity	NPD3618	Phase 1
0.8125	Intermediate Similarity	NPD7748	Approved
0.809	Intermediate Similarity	NPD4695	Discontinued
0.8085	Intermediate Similarity	NPD5328	Approved
0.7959	Intermediate Similarity	NPD4697	Phase 3
0.7959	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5221	Approved
0.7959	Intermediate Similarity	NPD5222	Approved
0.7935	Intermediate Similarity	NPD4786	Approved
0.7917	Intermediate Similarity	NPD6079	Approved
0.7912	Intermediate Similarity	NPD3667	Approved
0.7889	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4755	Approved
0.7879	Intermediate Similarity	NPD5173	Approved
0.7879	Intermediate Similarity	NPD7902	Approved
0.7742	Intermediate Similarity	NPD3133	Approved
0.7742	Intermediate Similarity	NPD3665	Phase 1
0.7742	Intermediate Similarity	NPD3666	Approved
0.7723	Intermediate Similarity	NPD5285	Approved
0.7723	Intermediate Similarity	NPD5286	Approved
0.7723	Intermediate Similarity	NPD4700	Approved
0.7723	Intermediate Similarity	NPD4696	Approved
0.7708	Intermediate Similarity	NPD4753	Phase 2
0.7667	Intermediate Similarity	NPD3617	Approved
0.7653	Intermediate Similarity	NPD4202	Approved
0.7647	Intermediate Similarity	NPD5223	Approved
0.7579	Intermediate Similarity	NPD5280	Approved
0.7579	Intermediate Similarity	NPD4694	Approved
0.7576	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7900	Approved
0.7573	Intermediate Similarity	NPD5225	Approved
0.7573	Intermediate Similarity	NPD5226	Approved
0.7573	Intermediate Similarity	NPD4633	Approved
0.7573	Intermediate Similarity	NPD5224	Approved
0.7573	Intermediate Similarity	NPD5211	Phase 2
0.7524	Intermediate Similarity	NPD7128	Approved
0.7524	Intermediate Similarity	NPD6402	Approved
0.7524	Intermediate Similarity	NPD5739	Approved
0.7524	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.7474	Intermediate Similarity	NPD5329	Approved
0.7429	Intermediate Similarity	NPD5141	Approved
0.7396	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7645	Phase 2
0.7383	Intermediate Similarity	NPD6881	Approved
0.7383	Intermediate Similarity	NPD6899	Approved
0.7383	Intermediate Similarity	NPD7320	Approved
0.7368	Intermediate Similarity	NPD3668	Phase 3
0.7368	Intermediate Similarity	NPD4197	Approved
0.7358	Intermediate Similarity	NPD4768	Approved
0.7358	Intermediate Similarity	NPD4767	Approved
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.7327	Intermediate Similarity	NPD4629	Approved
0.7327	Intermediate Similarity	NPD5210	Approved
0.7315	Intermediate Similarity	NPD6372	Approved
0.7315	Intermediate Similarity	NPD6373	Approved
0.73	Intermediate Similarity	NPD6399	Phase 3
0.729	Intermediate Similarity	NPD5697	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7248	Intermediate Similarity	NPD7102	Approved
0.7248	Intermediate Similarity	NPD7290	Approved
0.7248	Intermediate Similarity	NPD6883	Approved
0.7245	Intermediate Similarity	NPD6672	Approved
0.7245	Intermediate Similarity	NPD5737	Approved
0.7222	Intermediate Similarity	NPD6011	Approved
0.7222	Intermediate Similarity	NPD5168	Approved
0.7222	Intermediate Similarity	NPD5128	Approved
0.7222	Intermediate Similarity	NPD4730	Approved
0.7222	Intermediate Similarity	NPD4729	Approved
0.7216	Intermediate Similarity	NPD5690	Phase 2
0.72	Intermediate Similarity	NPD6411	Approved
0.7182	Intermediate Similarity	NPD6649	Approved
0.7182	Intermediate Similarity	NPD6617	Approved
0.7182	Intermediate Similarity	NPD6847	Approved
0.7182	Intermediate Similarity	NPD6650	Approved
0.7182	Intermediate Similarity	NPD8130	Phase 1
0.7182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6869	Approved
0.7158	Intermediate Similarity	NPD4223	Phase 3
0.7158	Intermediate Similarity	NPD4221	Approved
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7156	Intermediate Similarity	NPD6012	Approved
0.7156	Intermediate Similarity	NPD6013	Approved
0.7156	Intermediate Similarity	NPD6014	Approved
0.7129	Intermediate Similarity	NPD5133	Approved
0.7117	Intermediate Similarity	NPD8297	Approved
0.7117	Intermediate Similarity	NPD6882	Approved
0.7113	Intermediate Similarity	NPD1696	Phase 3
0.7113	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4634	Approved
0.7091	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5247	Approved
0.7091	Intermediate Similarity	NPD5250	Approved
0.7091	Intermediate Similarity	NPD5135	Approved
0.7091	Intermediate Similarity	NPD5248	Approved
0.7091	Intermediate Similarity	NPD5251	Approved
0.7091	Intermediate Similarity	NPD5169	Approved
0.7091	Intermediate Similarity	NPD5249	Phase 3
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.7071	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7146	Approved
0.7041	Intermediate Similarity	NPD5330	Approved
0.7041	Intermediate Similarity	NPD6409	Approved
0.7041	Intermediate Similarity	NPD6684	Approved
0.7041	Intermediate Similarity	NPD7521	Approved
0.7041	Intermediate Similarity	NPD7334	Approved
0.703	Intermediate Similarity	NPD5284	Approved
0.703	Intermediate Similarity	NPD6050	Approved
0.703	Intermediate Similarity	NPD5281	Approved
0.7027	Intermediate Similarity	NPD5217	Approved
0.7027	Intermediate Similarity	NPD5215	Approved
0.7027	Intermediate Similarity	NPD5216	Approved
0.7027	Intermediate Similarity	NPD5127	Approved
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3573	Approved
0.6957	Remote Similarity	NPD6942	Approved
0.6957	Remote Similarity	NPD7339	Approved
0.6952	Remote Similarity	NPD7638	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6947	Remote Similarity	NPD7525	Registered
0.6931	Remote Similarity	NPD5692	Phase 3
0.693	Remote Similarity	NPD6868	Approved
0.6907	Remote Similarity	NPD4788	Approved
0.6903	Remote Similarity	NPD4632	Approved
0.69	Remote Similarity	NPD6903	Approved
0.69	Remote Similarity	NPD4518	Approved
0.6887	Remote Similarity	NPD7639	Approved
0.6887	Remote Similarity	NPD7640	Approved
0.6882	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7115	Discovery
0.6869	Remote Similarity	NPD4623	Approved
0.6869	Remote Similarity	NPD4690	Approved
0.6869	Remote Similarity	NPD4519	Discontinued
0.6869	Remote Similarity	NPD4693	Phase 3
0.6869	Remote Similarity	NPD4138	Approved
0.6869	Remote Similarity	NPD5205	Approved
0.6869	Remote Similarity	NPD4689	Approved
0.6869	Remote Similarity	NPD4688	Approved
0.6863	Remote Similarity	NPD5694	Approved
0.6848	Remote Similarity	NPD5733	Approved
0.6847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5167	Approved
0.6832	Remote Similarity	NPD6673	Approved
0.6832	Remote Similarity	NPD6080	Approved
0.6832	Remote Similarity	NPD6904	Approved
0.6818	Remote Similarity	NPD6412	Phase 2
0.681	Remote Similarity	NPD6335	Approved
0.6807	Remote Similarity	NPD8328	Phase 3
0.6783	Remote Similarity	NPD6274	Approved
0.6774	Remote Similarity	NPD8264	Approved
0.6765	Remote Similarity	NPD4096	Approved
0.6762	Remote Similarity	NPD7732	Phase 3
0.6752	Remote Similarity	NPD7100	Approved
0.6752	Remote Similarity	NPD7101	Approved
0.6724	Remote Similarity	NPD6009	Approved
0.6724	Remote Similarity	NPD6317	Approved
0.6699	Remote Similarity	NPD8035	Phase 2
0.6699	Remote Similarity	NPD8034	Phase 2
0.6695	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6909	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.663	Remote Similarity	NPD5276	Approved
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4137	Phase 3
0.6593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6370	Approved
0.6581	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6008	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6542	Remote Similarity	NPD5959	Approved
0.6538	Remote Similarity	NPD5693	Phase 1
0.6535	Remote Similarity	NPD6098	Approved
0.6531	Remote Similarity	NPD4692	Approved
0.6531	Remote Similarity	NPD4139	Approved
0.6531	Remote Similarity	NPD8028	Phase 2
0.6529	Remote Similarity	NPD7604	Phase 2
0.6526	Remote Similarity	NPD6933	Approved
0.6526	Remote Similarity	NPD6117	Approved
0.6522	Remote Similarity	NPD4789	Approved
0.6522	Remote Similarity	NPD4747	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