NPASS Compound

Structure

NPC3732 OpenBabel07101718302D 22 24 0 0 1 0 0 0 0 0999 V2000 -3.8321 -1.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7664 1.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2665 -0.8635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5328 -1.7700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2993 -0.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6519 0.2011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8321 1.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2155 -0.1832 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2993 -1.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7664 -1.3275 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7664 -1.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7664 -0.4425 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5328 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7664 -0.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8321 2.2125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9819 0.2593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.6550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6106 0.6406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0657 -1.7700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5328 0.8850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 9 1 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 6 0 0 0 9 21 1 0 0 0 0 10 3 1 1 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 6 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.13
Volume:	301.818
LogP:	0.783
LogD:	0.761
LogS:	-3.873
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	4.773
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.166
MDCK Permeability:	5.972425060463138e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.689
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.903
Plasma Protein Binding (PPB):	41.91802978515625%
Volume Distribution (VD):	0.91
Pgp-substrate:	26.664081573486328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.731
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.488
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.571
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.458

ADMET: Excretion

Clearance (CL):	5.704
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.171
AMES Toxicity:	0.399
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.341
Carcinogencity:	0.085
Eye Corrosion:	0.004
Eye Irritation:	0.118
Respiratory Toxicity:	0.275

Download Data

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

Natural Product: NPC3732

Natural Product ID:	NPC3732
*Common Name:**	KKVJAMUGDMBKBM-ISTPORRPSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-(5R,7R,9R,11S)-Herbarone
Standard InCHIKey:	KKVJAMUGDMBKBM-ISTPORRPSA-N
Standard InCHI:	InChI=1S/C16H20O6/c1-21-9-4-11-14(13(5-9)22-2)16(20)6-8(18)3-10(15(11)19)12(16)7-17/h4-5,8,10,12,17-18,20H,3,6-7H2,1-2H3/t8-,10-,12-,16-/m1/s1
SMILES:	COc1cc2c(c(c1)OC)[C@]1(C[C@@H](C[C@H]([C@H]1CO)C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152642
PubChem CID:	71449455
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO5686	Torula herbarum	Species	Torulaceae	Eukaryota	Sea Hare Associated Fungus	n.a.	n.a.	PMID[23043498]
NPO5686	Torula herbarum	Species	Torulaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2351	Cell Line	MG-63	Homo sapiens	IC50	>	97400.0	nM	PMID[470469]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	97400.0	nM	PMID[470469]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	97400.0	nM	PMID[470469]

☑ 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 NPC3732 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	346
0.1-0.2	1346
0.2-0.3	2771
0.3-0.4	6702
0.4-0.5	11479
0.5-0.6	4446
0.6-0.7	5544
0.7-0.8	8610
0.8-0.85	1312
0.85-0.9	125
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.951	High Similarity	NPC225854
0.9379	High Similarity	NPC180944
0.9247	High Similarity	NPC268992
0.9247	High Similarity	NPC113608
0.9247	High Similarity	NPC470338
0.9247	High Similarity	NPC470337
0.9247	High Similarity	NPC51824
0.9247	High Similarity	NPC470340
0.9178	High Similarity	NPC470569
0.9122	High Similarity	NPC68727
0.911	High Similarity	NPC470568
0.9048	High Similarity	NPC46882
0.9048	High Similarity	NPC132990
0.898	High Similarity	NPC255641
0.898	High Similarity	NPC290954
0.898	High Similarity	NPC147735
0.8958	High Similarity	NPC19896
0.894	High Similarity	NPC470339
0.8926	High Similarity	NPC155686
0.8912	High Similarity	NPC329933
0.8904	High Similarity	NPC289042
0.8904	High Similarity	NPC245584
0.8904	High Similarity	NPC56433
0.8904	High Similarity	NPC118027
0.8904	High Similarity	NPC190648
0.8904	High Similarity	NPC34802
0.8904	High Similarity	NPC312929
0.8904	High Similarity	NPC126767
0.8882	High Similarity	NPC472055
0.8859	High Similarity	NPC40356
0.8859	High Similarity	NPC154683
0.8819	High Similarity	NPC49108
0.8816	High Similarity	NPC4950
0.8816	High Similarity	NPC226287
0.8816	High Similarity	NPC218818
0.8792	High Similarity	NPC149526
0.8792	High Similarity	NPC478148
0.8792	High Similarity	NPC474417
0.8776	High Similarity	NPC77903
0.8776	High Similarity	NPC17101
0.8767	High Similarity	NPC478019
0.8767	High Similarity	NPC34482
0.8767	High Similarity	NPC49282
0.8759	High Similarity	NPC215451
0.8759	High Similarity	NPC277369
0.8759	High Similarity	NPC167663
0.8758	High Similarity	NPC155302
0.8758	High Similarity	NPC472618
0.8758	High Similarity	NPC161947
0.875	High Similarity	NPC158542
0.8733	High Similarity	NPC87708
0.8732	High Similarity	NPC24394
0.8725	High Similarity	NPC294646
0.8716	High Similarity	NPC146388
0.8716	High Similarity	NPC472841
0.871	High Similarity	NPC100849
0.8707	High Similarity	NPC470570
0.8707	High Similarity	NPC469758
0.8701	High Similarity	NPC87431
0.8699	High Similarity	NPC48762
0.8699	High Similarity	NPC475201
0.8693	High Similarity	NPC239118
0.8693	High Similarity	NPC324736
0.8693	High Similarity	NPC472617
0.8693	High Similarity	NPC186113
0.869	High Similarity	NPC126534
0.869	High Similarity	NPC232021
0.869	High Similarity	NPC40118
0.8684	High Similarity	NPC472050
0.8684	High Similarity	NPC164427
0.8675	High Similarity	NPC208806
0.8675	High Similarity	NPC135522
0.8667	High Similarity	NPC232645
0.8667	High Similarity	NPC78505
0.8667	High Similarity	NPC230848
0.8667	High Similarity	NPC72958
0.8658	High Similarity	NPC80370
0.8658	High Similarity	NPC65775
0.8658	High Similarity	NPC10027
0.8654	High Similarity	NPC472049
0.8645	High Similarity	NPC473961
0.8639	High Similarity	NPC469764
0.8636	High Similarity	NPC470810
0.863	High Similarity	NPC84266
0.863	High Similarity	NPC472006
0.8627	High Similarity	NPC272196
0.8621	High Similarity	NPC253822
0.8621	High Similarity	NPC265178
0.8618	High Similarity	NPC226656
0.8618	High Similarity	NPC66508
0.8611	High Similarity	NPC472368
0.8609	High Similarity	NPC474843
0.86	High Similarity	NPC202595
0.8591	High Similarity	NPC2569
0.8591	High Similarity	NPC172329
0.8571	High Similarity	NPC21599
0.8571	High Similarity	NPC475705
0.8571	High Similarity	NPC51887
0.8571	High Similarity	NPC471451
0.8571	High Similarity	NPC117836
0.8571	High Similarity	NPC193703
0.8571	High Similarity	NPC476178
0.8562	High Similarity	NPC470087
0.8562	High Similarity	NPC94076
0.8562	High Similarity	NPC469579
0.8562	High Similarity	NPC135524
0.8562	High Similarity	NPC26051
0.8562	High Similarity	NPC55832
0.8562	High Similarity	NPC268204
0.8562	High Similarity	NPC18714
0.8562	High Similarity	NPC182255
0.8562	High Similarity	NPC321980
0.8562	High Similarity	NPC103752
0.8562	High Similarity	NPC52789
0.8553	High Similarity	NPC107109
0.8553	High Similarity	NPC303950
0.8553	High Similarity	NPC169990
0.8553	High Similarity	NPC210942
0.8553	High Similarity	NPC93552
0.8553	High Similarity	NPC329844
0.8552	High Similarity	NPC477956
0.8552	High Similarity	NPC109007
0.8552	High Similarity	NPC472366
0.8552	High Similarity	NPC109232
0.8552	High Similarity	NPC470211
0.8552	High Similarity	NPC201541
0.8544	High Similarity	NPC470341
0.8544	High Similarity	NPC324522
0.8544	High Similarity	NPC472058
0.8544	High Similarity	NPC105414
0.8544	High Similarity	NPC234497
0.8543	High Similarity	NPC476553
0.8543	High Similarity	NPC207346
0.8543	High Similarity	NPC470675
0.8543	High Similarity	NPC473131
0.8543	High Similarity	NPC476552
0.8543	High Similarity	NPC476551
0.8543	High Similarity	NPC46564
0.8542	High Similarity	NPC23870
0.8533	High Similarity	NPC4423
0.8533	High Similarity	NPC97028
0.8533	High Similarity	NPC288036
0.8533	High Similarity	NPC158338
0.8533	High Similarity	NPC146014
0.8533	High Similarity	NPC65589
0.8533	High Similarity	NPC97029
0.8533	High Similarity	NPC100985
0.8533	High Similarity	NPC77325
0.8531	High Similarity	NPC141934
0.8523	High Similarity	NPC222298
0.8523	High Similarity	NPC162751
0.8523	High Similarity	NPC51070
0.8523	High Similarity	NPC71055
0.8523	High Similarity	NPC52161
0.8521	High Similarity	NPC27643
0.8516	High Similarity	NPC284495
0.8514	High Similarity	NPC476055
0.8514	High Similarity	NPC471523
0.8514	High Similarity	NPC471473
0.8514	High Similarity	NPC471524
0.8511	High Similarity	NPC128348
0.8511	High Similarity	NPC309717
0.8511	High Similarity	NPC66384
0.8511	High Similarity	NPC189106
0.8511	High Similarity	NPC112192
0.8511	High Similarity	NPC164236
0.8506	High Similarity	NPC44199
0.8506	High Similarity	NPC199463
0.8506	High Similarity	NPC37543
0.8503	High Similarity	NPC51106
0.8503	High Similarity	NPC469542
0.8503	High Similarity	NPC297600
0.8503	High Similarity	NPC310340
0.8497	Intermediate Similarity	NPC175192
0.8493	Intermediate Similarity	NPC305845
0.8493	Intermediate Similarity	NPC213659
0.8493	Intermediate Similarity	NPC259166
0.8493	Intermediate Similarity	NPC101366
0.8493	Intermediate Similarity	NPC204045
0.8493	Intermediate Similarity	NPC172250
0.8493	Intermediate Similarity	NPC144118
0.8493	Intermediate Similarity	NPC80962
0.8493	Intermediate Similarity	NPC48624
0.8493	Intermediate Similarity	NPC326109
0.8493	Intermediate Similarity	NPC204985
0.8493	Intermediate Similarity	NPC1704
0.8493	Intermediate Similarity	NPC215311
0.8493	Intermediate Similarity	NPC67650
0.8493	Intermediate Similarity	NPC219917
0.8487	Intermediate Similarity	NPC43345
0.8487	Intermediate Similarity	NPC167903
0.8483	Intermediate Similarity	NPC90665
0.8483	Intermediate Similarity	NPC12175
0.8483	Intermediate Similarity	NPC279668
0.8483	Intermediate Similarity	NPC55162
0.8483	Intermediate Similarity	NPC1268
0.8483	Intermediate Similarity	NPC278323
0.8483	Intermediate Similarity	NPC21350
0.8483	Intermediate Similarity	NPC309154
0.8481	Intermediate Similarity	NPC125465

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 NPC3732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	892
0.2-0.3	1482
0.3-0.4	2456
0.4-0.5	2119
0.5-0.6	1147
0.6-0.7	558
0.7-0.8	181
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8312	Intermediate Similarity	NPD7819	Suspended
0.8276	Intermediate Similarity	NPD1510	Phase 2
0.8247	Intermediate Similarity	NPD37	Approved
0.8243	Intermediate Similarity	NPD3750	Approved
0.8231	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6959	Discontinued
0.8151	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5844	Phase 1
0.8146	Intermediate Similarity	NPD2532	Approved
0.8146	Intermediate Similarity	NPD2534	Approved
0.8146	Intermediate Similarity	NPD2533	Approved
0.8141	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1607	Approved
0.8137	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD1240	Approved
0.8121	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD4380	Phase 2
0.8108	Intermediate Similarity	NPD1549	Phase 2
0.8095	Intermediate Similarity	NPD6100	Approved
0.8095	Intermediate Similarity	NPD6099	Approved
0.8095	Intermediate Similarity	NPD2796	Approved
0.8089	Intermediate Similarity	NPD4966	Approved
0.8089	Intermediate Similarity	NPD4967	Phase 2
0.8089	Intermediate Similarity	NPD4965	Approved
0.8077	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD3748	Approved
0.8026	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7411	Suspended
0.7933	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1934	Approved
0.7881	Intermediate Similarity	NPD7003	Approved
0.7881	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6234	Discontinued
0.7862	Intermediate Similarity	NPD7768	Phase 2
0.7857	Intermediate Similarity	NPD6273	Approved
0.7852	Intermediate Similarity	NPD2935	Discontinued
0.7848	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5494	Approved
0.7821	Intermediate Similarity	NPD3226	Approved
0.7812	Intermediate Similarity	NPD3749	Approved
0.7812	Intermediate Similarity	NPD7075	Discontinued
0.7785	Intermediate Similarity	NPD6801	Discontinued
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD1470	Approved
0.775	Intermediate Similarity	NPD3882	Suspended
0.7744	Intermediate Similarity	NPD6166	Phase 2
0.7744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3764	Approved
0.774	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2801	Approved
0.7727	Intermediate Similarity	NPD7390	Discontinued
0.7724	Intermediate Similarity	NPD4908	Phase 1
0.7702	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5402	Approved
0.7682	Intermediate Similarity	NPD2346	Discontinued
0.7679	Intermediate Similarity	NPD6559	Discontinued
0.7677	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4625	Phase 3
0.7667	Intermediate Similarity	NPD2799	Discontinued
0.7658	Intermediate Similarity	NPD6599	Discontinued
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7651	Intermediate Similarity	NPD7228	Approved
0.7651	Intermediate Similarity	NPD6651	Approved
0.7636	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4749	Approved
0.7619	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1551	Phase 2
0.7613	Intermediate Similarity	NPD1511	Approved
0.7613	Intermediate Similarity	NPD6799	Approved
0.7606	Intermediate Similarity	NPD1201	Approved
0.7595	Intermediate Similarity	NPD7458	Discontinued
0.7586	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2798	Approved
0.7584	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5124	Phase 1
0.7582	Intermediate Similarity	NPD2800	Approved
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5403	Approved
0.7569	Intermediate Similarity	NPD1876	Approved
0.7569	Intermediate Similarity	NPD1283	Approved
0.7518	Intermediate Similarity	NPD1651	Approved
0.7516	Intermediate Similarity	NPD5760	Phase 2
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD5761	Phase 2
0.7516	Intermediate Similarity	NPD1512	Approved
0.7515	Intermediate Similarity	NPD5711	Approved
0.7515	Intermediate Similarity	NPD5710	Approved
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7485	Intermediate Similarity	NPD8312	Approved
0.7485	Intermediate Similarity	NPD8313	Approved
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7469	Intermediate Similarity	NPD3817	Phase 2
0.7467	Intermediate Similarity	NPD230	Phase 1
0.7465	Intermediate Similarity	NPD4626	Approved
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7455	Intermediate Similarity	NPD7199	Phase 2
0.7452	Intermediate Similarity	NPD5401	Approved
0.744	Intermediate Similarity	NPD3751	Discontinued
0.7434	Intermediate Similarity	NPD4308	Phase 3
0.7432	Intermediate Similarity	NPD3027	Phase 3
0.7431	Intermediate Similarity	NPD3972	Approved
0.74	Intermediate Similarity	NPD943	Approved
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2797	Approved
0.7396	Intermediate Similarity	NPD7054	Approved
0.7396	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3268	Approved
0.7368	Intermediate Similarity	NPD7240	Approved
0.7362	Intermediate Similarity	NPD4288	Approved
0.7361	Intermediate Similarity	NPD1281	Approved
0.7353	Intermediate Similarity	NPD7472	Approved
0.7343	Intermediate Similarity	NPD3019	Approved
0.7342	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6797	Phase 2
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7293	Intermediate Similarity	NPD6776	Approved
0.7293	Intermediate Similarity	NPD6777	Approved
0.7293	Intermediate Similarity	NPD6781	Approved
0.7293	Intermediate Similarity	NPD6782	Approved
0.7293	Intermediate Similarity	NPD6778	Approved
0.7293	Intermediate Similarity	NPD6779	Approved
0.7293	Intermediate Similarity	NPD6780	Approved
0.7285	Intermediate Similarity	NPD1613	Approved
0.7285	Intermediate Similarity	NPD4140	Approved
0.7285	Intermediate Similarity	NPD2979	Phase 3
0.7285	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2438	Suspended
0.7273	Intermediate Similarity	NPD5691	Approved
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7267	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7251	Discontinued
0.7262	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8150	Discontinued
0.7257	Intermediate Similarity	NPD8434	Phase 2
0.725	Intermediate Similarity	NPD920	Approved
0.7246	Intermediate Similarity	NPD8127	Discontinued
0.7244	Intermediate Similarity	NPD1243	Approved
0.7244	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7177	Discontinued
0.7226	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2344	Approved
0.7225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7808	Phase 3
0.7222	Intermediate Similarity	NPD2932	Approved
0.7219	Intermediate Similarity	NPD8032	Phase 2
0.7213	Intermediate Similarity	NPD6823	Phase 2
0.7209	Intermediate Similarity	NPD5953	Discontinued
0.7208	Intermediate Similarity	NPD7033	Discontinued
0.7208	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1548	Phase 1
0.7197	Intermediate Similarity	NPD8166	Discontinued
0.7192	Intermediate Similarity	NPD1608	Approved
0.719	Intermediate Similarity	NPD4097	Suspended
0.7181	Intermediate Similarity	NPD2861	Phase 2
0.7179	Intermediate Similarity	NPD2424	Discontinued
0.7174	Intermediate Similarity	NPD7697	Approved
0.7174	Intermediate Similarity	NPD7435	Discontinued
0.7174	Intermediate Similarity	NPD7696	Phase 3
0.7174	Intermediate Similarity	NPD7698	Approved
0.7171	Intermediate Similarity	NPD2238	Phase 2
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.7171	Intermediate Similarity	NPD4307	Phase 2
0.7171	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3620	Phase 2
0.717	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8151	Discontinued
0.716	Intermediate Similarity	NPD3926	Phase 2
0.716	Intermediate Similarity	NPD2651	Approved
0.716	Intermediate Similarity	NPD2649	Approved
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7134	Intermediate Similarity	NPD2654	Approved
0.7133	Intermediate Similarity	NPD6832	Phase 2
0.7125	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5735	Approved
0.7124	Intermediate Similarity	NPD6355	Discontinued
0.7123	Intermediate Similarity	NPD422	Phase 1
0.7115	Intermediate Similarity	NPD6006	Clinical (unspecified phase)

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