NPASS Compound

Structure

NPC472600 OpenBabel07101719142D 21 22 0 0 1 0 0 0 0 0999 V2000 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -1.7321 -1.0000 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 0.8660 -1.5000 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 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 11 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 8 1 1 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.17
Volume:	310.09
LogP:	5.433
LogD:	3.825
LogS:	-4.109
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	3.048
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.769
MDCK Permeability:	2.8539869163068943e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.648

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.514
Plasma Protein Binding (PPB):	98.49568939208984%
Volume Distribution (VD):	1.154
Pgp-substrate:	1.7429592609405518%

ADMET: Metabolism

CYP1A2-inhibitor:	0.895
CYP1A2-substrate:	0.574
CYP2C19-inhibitor:	0.821
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.559
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.401
CYP3A4-inhibitor:	0.315
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	9.363
Half-life (T1/2):	0.555

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.65
AMES Toxicity:	0.219
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.803
Carcinogencity:	0.34
Eye Corrosion:	0.167
Eye Irritation:	0.967
Respiratory Toxicity:	0.742

Download Data

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

Natural Product: NPC472600

Natural Product ID:	NPC472600
*Common Name:**	PLJYMTQRTVQXHS-GFCCVEGCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PLJYMTQRTVQXHS-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C17H24O4/c1-3-4-5-6-7-8-12-9-13-11(2)14(18)10-15(19)16(13)17(20)21-12/h10,12,18-19H,3-9H2,1-2H3/t12-/m1/s1
SMILES:	CCCCCCC[C@H]1OC(=O)c2c(C1)c(C)c(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3580979
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid 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
NPO32981	cadophora sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[26035018]
NPO41397	Cosmospora sp. + Magnaporthe oryzae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[35054969]

☑ 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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[458803]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	40.0	ug.mL-1	PMID[458803]

☑ 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 NPC472600 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	321
0.1-0.2	1408
0.2-0.3	3372
0.3-0.4	7682
0.4-0.5	11039
0.5-0.6	3953
0.6-0.7	6650
0.7-0.8	6290
0.8-0.85	1587
0.85-0.9	285
0.9-0.95	88
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472601
0.9925	High Similarity	NPC472605
0.9925	High Similarity	NPC472603
0.9925	High Similarity	NPC472604
0.9779	High Similarity	NPC472610
0.9779	High Similarity	NPC159721
0.9776	High Similarity	NPC88269
0.9708	High Similarity	NPC151607
0.9708	High Similarity	NPC42540
0.9701	High Similarity	NPC472602
0.9635	High Similarity	NPC471731
0.9632	High Similarity	NPC53649
0.9627	High Similarity	NPC70380
0.9568	High Similarity	NPC473023
0.9562	High Similarity	NPC471733
0.9556	High Similarity	NPC212693
0.9556	High Similarity	NPC94248
0.9556	High Similarity	NPC191835
0.9552	High Similarity	NPC235115
0.9481	High Similarity	NPC194579
0.9412	High Similarity	NPC33144
0.9412	High Similarity	NPC221104
0.9412	High Similarity	NPC478200
0.9407	High Similarity	NPC50455
0.9407	High Similarity	NPC291454
0.9407	High Similarity	NPC472599
0.9362	High Similarity	NPC471734
0.9353	High Similarity	NPC478202
0.9353	High Similarity	NPC469542
0.9348	High Similarity	NPC158634
0.9348	High Similarity	NPC478217
0.9348	High Similarity	NPC67650
0.9348	High Similarity	NPC313123
0.9348	High Similarity	NPC1704
0.9343	High Similarity	NPC32360
0.9343	High Similarity	NPC105456
0.9343	High Similarity	NPC275356
0.9343	High Similarity	NPC139634
0.9338	High Similarity	NPC71256
0.9328	High Similarity	NPC153783
0.9291	High Similarity	NPC471735
0.9281	High Similarity	NPC82913
0.9281	High Similarity	NPC469579
0.9275	High Similarity	NPC158472
0.9275	High Similarity	NPC155205
0.9265	High Similarity	NPC158481
0.9265	High Similarity	NPC156967
0.9254	High Similarity	NPC476389
0.922	High Similarity	NPC473692
0.9214	High Similarity	NPC51106
0.9214	High Similarity	NPC472006
0.9209	High Similarity	NPC472035
0.9209	High Similarity	NPC478201
0.9209	High Similarity	NPC470842
0.9209	High Similarity	NPC37530
0.9203	High Similarity	NPC268052
0.9197	High Similarity	NPC149372
0.9197	High Similarity	NPC474849
0.9197	High Similarity	NPC245058
0.9197	High Similarity	NPC178467
0.9197	High Similarity	NPC474771
0.9197	High Similarity	NPC65837
0.9191	High Similarity	NPC142027
0.9191	High Similarity	NPC27407
0.9179	High Similarity	NPC219892
0.9179	High Similarity	NPC189823
0.9143	High Similarity	NPC322112
0.9143	High Similarity	NPC474385
0.9137	High Similarity	NPC99441
0.9137	High Similarity	NPC64664
0.913	High Similarity	NPC475974
0.9118	High Similarity	NPC175943
0.9085	High Similarity	NPC83272
0.9071	High Similarity	NPC475730
0.9071	High Similarity	NPC244923
0.9058	High Similarity	NPC301915
0.9058	High Similarity	NPC261292
0.9058	High Similarity	NPC135837
0.9037	High Similarity	NPC214702
0.9037	High Similarity	NPC470831
0.9028	High Similarity	NPC221352
0.9021	High Similarity	NPC260946
0.9021	High Similarity	NPC107625
0.9021	High Similarity	NPC225173
0.9021	High Similarity	NPC163846
0.9014	High Similarity	NPC126882
0.9014	High Similarity	NPC86373
0.9014	High Similarity	NPC277426
0.9014	High Similarity	NPC478203
0.9014	High Similarity	NPC210966
0.9014	High Similarity	NPC280404
0.9014	High Similarity	NPC210425
0.9007	High Similarity	NPC250755
0.9	High Similarity	NPC165172
0.9	High Similarity	NPC168471
0.8993	High Similarity	NPC9121
0.8993	High Similarity	NPC472403
0.8993	High Similarity	NPC177307
0.898	High Similarity	NPC472799
0.8978	High Similarity	NPC475645
0.8973	High Similarity	NPC70016
0.8973	High Similarity	NPC215921
0.8966	High Similarity	NPC233267
0.8966	High Similarity	NPC291049
0.8966	High Similarity	NPC270160
0.8966	High Similarity	NPC237440
0.8963	High Similarity	NPC296158
0.8958	High Similarity	NPC53362
0.8958	High Similarity	NPC125801
0.8958	High Similarity	NPC166583
0.8951	High Similarity	NPC257558
0.8951	High Similarity	NPC134621
0.8951	High Similarity	NPC472034
0.8929	High Similarity	NPC92655
0.8929	High Similarity	NPC247409
0.8929	High Similarity	NPC474655
0.8929	High Similarity	NPC52358
0.8913	High Similarity	NPC290803
0.8913	High Similarity	NPC182496
0.8913	High Similarity	NPC180905
0.8912	High Similarity	NPC273483
0.8905	High Similarity	NPC180261
0.8905	High Similarity	NPC37299
0.8904	High Similarity	NPC179178
0.8904	High Similarity	NPC150928
0.8897	High Similarity	NPC105415
0.8897	High Similarity	NPC240622
0.8897	High Similarity	NPC471641
0.8897	High Similarity	NPC471642
0.8897	High Similarity	NPC37139
0.8897	High Similarity	NPC240253
0.8889	High Similarity	NPC237208
0.8889	High Similarity	NPC472033
0.8889	High Similarity	NPC470570
0.8881	High Similarity	NPC66404
0.8881	High Similarity	NPC95123
0.8851	High Similarity	NPC470102
0.8849	High Similarity	NPC118919
0.8844	High Similarity	NPC232645
0.8844	High Similarity	NPC72958
0.8844	High Similarity	NPC133856
0.8841	High Similarity	NPC474394
0.8836	High Similarity	NPC476684
0.8836	High Similarity	NPC77325
0.8836	High Similarity	NPC4423
0.8828	High Similarity	NPC472036
0.8828	High Similarity	NPC210320
0.8828	High Similarity	NPC476463
0.8828	High Similarity	NPC8817
0.8824	High Similarity	NPC17840
0.8824	High Similarity	NPC247477
0.8819	High Similarity	NPC34482
0.8819	High Similarity	NPC312789
0.8819	High Similarity	NPC29577
0.8819	High Similarity	NPC75694
0.8811	High Similarity	NPC471639
0.8811	High Similarity	NPC471643
0.8811	High Similarity	NPC354984
0.8803	High Similarity	NPC149533
0.8803	High Similarity	NPC90411
0.8792	High Similarity	NPC149618
0.8792	High Similarity	NPC82592
0.8792	High Similarity	NPC16082
0.8792	High Similarity	NPC89625
0.8784	High Similarity	NPC217447
0.8784	High Similarity	NPC87708
0.8784	High Similarity	NPC115249
0.8784	High Similarity	NPC167903
0.8777	High Similarity	NPC278375
0.8777	High Similarity	NPC470844
0.8776	High Similarity	NPC469619
0.8776	High Similarity	NPC158866
0.8776	High Similarity	NPC469670
0.8776	High Similarity	NPC119929
0.8776	High Similarity	NPC56204
0.8776	High Similarity	NPC472891
0.8768	High Similarity	NPC470988
0.8767	High Similarity	NPC73411
0.8767	High Similarity	NPC215711
0.8759	High Similarity	NPC187282
0.8759	High Similarity	NPC267509
0.8759	High Similarity	NPC290133
0.8759	High Similarity	NPC470357
0.8759	High Similarity	NPC24136
0.875	High Similarity	NPC48762
0.8741	High Similarity	NPC105648
0.8733	High Similarity	NPC150227
0.8733	High Similarity	NPC472050
0.8731	High Similarity	NPC262671
0.8731	High Similarity	NPC201728
0.8725	High Similarity	NPC471695
0.8725	High Similarity	NPC137301
0.8725	High Similarity	NPC281477
0.8725	High Similarity	NPC192189
0.8723	High Similarity	NPC197666
0.8723	High Similarity	NPC126739
0.8716	High Similarity	NPC200773
0.8716	High Similarity	NPC240768
0.8707	High Similarity	NPC84142
0.8705	High Similarity	NPC470984

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 NPC472600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	937
0.2-0.3	1734
0.3-0.4	2592
0.4-0.5	1936
0.5-0.6	1126
0.6-0.7	406
0.7-0.8	127
0.8-0.85	19
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD970	Clinical (unspecified phase)
0.8819	High Similarity	NPD2533	Approved
0.8819	High Similarity	NPD2534	Approved
0.8819	High Similarity	NPD2532	Approved
0.8725	High Similarity	NPD7819	Suspended
0.8387	Intermediate Similarity	NPD6959	Discontinued
0.8355	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD7075	Discontinued
0.8235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7411	Suspended
0.8217	Intermediate Similarity	NPD6232	Discontinued
0.8217	Intermediate Similarity	NPD5711	Approved
0.8217	Intermediate Similarity	NPD5710	Approved
0.8207	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4380	Phase 2
0.8151	Intermediate Similarity	NPD1549	Phase 2
0.8138	Intermediate Similarity	NPD2935	Discontinued
0.8112	Intermediate Similarity	NPD230	Phase 1
0.8069	Intermediate Similarity	NPD1510	Phase 2
0.8063	Intermediate Similarity	NPD7473	Discontinued
0.8052	Intermediate Similarity	NPD6801	Discontinued
0.8052	Intermediate Similarity	NPD1934	Approved
0.8042	Intermediate Similarity	NPD1240	Approved
0.8013	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7390	Discontinued
0.7973	Intermediate Similarity	NPD2800	Approved
0.7963	Intermediate Similarity	NPD5844	Phase 1
0.7931	Intermediate Similarity	NPD1607	Approved
0.7931	Intermediate Similarity	NPD6651	Approved
0.7919	Intermediate Similarity	NPD3750	Approved
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD5405	Approved
0.7891	Intermediate Similarity	NPD5404	Approved
0.7891	Intermediate Similarity	NPD5408	Approved
0.7891	Intermediate Similarity	NPD2796	Approved
0.7891	Intermediate Similarity	NPD5406	Approved
0.7881	Intermediate Similarity	NPD6799	Approved
0.7868	Intermediate Similarity	NPD9545	Approved
0.7848	Intermediate Similarity	NPD3749	Approved
0.7829	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6599	Discontinued
0.78	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1551	Phase 2
0.7736	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1243	Approved
0.7733	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD3817	Phase 2
0.7721	Intermediate Similarity	NPD9493	Approved
0.7673	Intermediate Similarity	NPD3882	Suspended
0.7671	Intermediate Similarity	NPD943	Approved
0.7669	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6166	Phase 2
0.7669	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2801	Approved
0.7658	Intermediate Similarity	NPD1465	Phase 2
0.7655	Intermediate Similarity	NPD3764	Approved
0.7647	Intermediate Similarity	NPD1511	Approved
0.764	Intermediate Similarity	NPD5494	Approved
0.7636	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3226	Approved
0.7605	Intermediate Similarity	NPD6559	Discontinued
0.76	Intermediate Similarity	NPD2346	Discontinued
0.759	Intermediate Similarity	NPD7074	Phase 3
0.7584	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD3748	Approved
0.7584	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4628	Phase 3
0.7552	Intermediate Similarity	NPD1164	Approved
0.7548	Intermediate Similarity	NPD1512	Approved
0.7545	Intermediate Similarity	NPD5953	Discontinued
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.753	Intermediate Similarity	NPD7286	Phase 2
0.753	Intermediate Similarity	NPD7054	Approved
0.7518	Intermediate Similarity	NPD1201	Approved
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7472	Approved
0.7485	Intermediate Similarity	NPD8150	Discontinued
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3818	Discontinued
0.7469	Intermediate Similarity	NPD919	Approved
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6797	Phase 2
0.7431	Intermediate Similarity	NPD1470	Approved
0.7415	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7251	Discontinued
0.7391	Intermediate Similarity	NPD5402	Approved
0.7389	Intermediate Similarity	NPD5403	Approved
0.7383	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5124	Phase 1
0.7376	Intermediate Similarity	NPD4626	Approved
0.7375	Intermediate Similarity	NPD37	Approved
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6234	Discontinued
0.7353	Intermediate Similarity	NPD7808	Phase 3
0.7346	Intermediate Similarity	NPD4967	Phase 2
0.7346	Intermediate Similarity	NPD4966	Approved
0.7346	Intermediate Similarity	NPD4965	Approved
0.7343	Intermediate Similarity	NPD9269	Phase 2
0.7343	Intermediate Similarity	NPD9717	Approved
0.7337	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7229	Phase 3
0.731	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD5691	Approved
0.7305	Intermediate Similarity	NPD9268	Approved
0.7297	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7261	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5401	Approved
0.7251	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1283	Approved
0.7237	Intermediate Similarity	NPD7033	Discontinued
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7226	Intermediate Similarity	NPD7003	Approved
0.7222	Intermediate Similarity	NPD1608	Approved
0.7214	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8313	Approved
0.7209	Intermediate Similarity	NPD8312	Approved
0.7205	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4060	Phase 1
0.72	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8151	Discontinued
0.7183	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2313	Discontinued
0.7181	Intermediate Similarity	NPD411	Approved
0.7179	Intermediate Similarity	NPD6190	Approved
0.717	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7199	Phase 2
0.7162	Intermediate Similarity	NPD4908	Phase 1
0.7161	Intermediate Similarity	NPD2654	Approved
0.716	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2344	Approved
0.7135	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD6534	Approved
0.7133	Intermediate Similarity	NPD6663	Approved
0.7132	Intermediate Similarity	NPD74	Approved
0.7132	Intermediate Similarity	NPD9266	Approved
0.7107	Intermediate Similarity	NPD6273	Approved
0.7104	Intermediate Similarity	NPD7435	Discontinued
0.7095	Intermediate Similarity	NPD5736	Approved
0.7089	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2979	Phase 3
0.7083	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7458	Discontinued
0.7078	Intermediate Similarity	NPD4476	Approved
0.7078	Intermediate Similarity	NPD4477	Approved
0.7078	Intermediate Similarity	NPD2438	Suspended
0.7075	Intermediate Similarity	NPD2797	Approved
0.7073	Intermediate Similarity	NPD4288	Approved
0.7073	Intermediate Similarity	NPD5353	Approved
0.7067	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3268	Approved
0.7066	Intermediate Similarity	NPD1247	Approved
0.7065	Intermediate Similarity	NPD8320	Phase 1
0.7065	Intermediate Similarity	NPD8319	Approved
0.7059	Intermediate Similarity	NPD9267	Approved
0.7059	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9264	Approved
0.7059	Intermediate Similarity	NPD9263	Approved
0.7059	Intermediate Similarity	NPD7177	Discontinued
0.7055	Intermediate Similarity	NPD4749	Approved
0.7039	Intermediate Similarity	NPD4360	Phase 2
0.7039	Intermediate Similarity	NPD4363	Phase 3
0.7034	Intermediate Similarity	NPD1281	Approved
0.7034	Intermediate Similarity	NPD1610	Phase 2
0.7033	Intermediate Similarity	NPD6780	Approved
0.7033	Intermediate Similarity	NPD6776	Approved
0.7033	Intermediate Similarity	NPD6777	Approved
0.7033	Intermediate Similarity	NPD6779	Approved
0.7033	Intermediate Similarity	NPD6781	Approved
0.7033	Intermediate Similarity	NPD6778	Approved
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6782	Approved
0.7032	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6005	Phase 3
0.7032	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6004	Phase 3
0.7032	Intermediate Similarity	NPD6002	Phase 3
0.7027	Intermediate Similarity	NPD2798	Approved
0.7027	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD520	Approved
0.7017	Intermediate Similarity	NPD7700	Phase 2
0.7017	Intermediate Similarity	NPD7699	Phase 2
0.7014	Intermediate Similarity	NPD17	Approved
0.7006	Intermediate Similarity	NPD8166	Discontinued
0.6982	Remote Similarity	NPD3926	Phase 2
0.6962	Remote Similarity	NPD2309	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