NPASS Compound

Structure

CID322021 OpenBabel06191716162D 23 24 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -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 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 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 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 -0.8660 -0.5000 0.0000 C 0 0 0 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 15 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 1 1 1 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 12 18 2 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.11
Volume:	319.761
LogP:	2.426
LogD:	2.375
LogS:	-3.585
# Rotatable Bonds:	5
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	2.818
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.802
MDCK Permeability:	1.2942441571794916e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.221
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	98.6251449584961%
Volume Distribution (VD):	0.508
Pgp-substrate:	1.5662537813186646%

ADMET: Metabolism

CYP1A2-inhibitor:	0.874
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.372
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.741
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.448
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.502

ADMET: Excretion

Clearance (CL):	9.152
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.648
AMES Toxicity:	0.351
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.23
Skin Sensitization:	0.7
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.882
Respiratory Toxicity:	0.385

Download Data

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

Natural Product: NPC322021

Natural Product ID:	NPC322021
*Common Name:**	Pterolinus E
IUPAC Name:	2-[(1R,2R)-1-hydroxy-1-(3-hydroxy-4-methoxyphenyl)propan-2-yl]-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	Pterolinus E
Standard InCHIKey:	AKHDQNNOJBGYAP-VVVCHXIZSA-N
Standard InCHI:	InChI=1S/C17H18O6/c1-9(11-7-14(20)16(23-3)8-12(11)18)17(21)10-4-5-15(22-2)13(19)6-10/h4-9,17,19,21H,1-3H3/t9-,17-/m1/s1
SMILES:	COC1=CC(=O)C(=CC1=O)[C@H]([C@H](c1ccc(c(c1)O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801602
PubChem CID:	53354911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	Heartwood	India	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[21784631]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	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	7

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6.96	ug.mL-1	PMID[474653]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	6.96	ug.mL-1	PMID[474653]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	6.96	ug.mL-1	PMID[474653]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6.96	ug.mL-1	PMID[474653]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	6.96	ug.mL-1	PMID[474653]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.96	ug.mL-1	PMID[474653]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.13	ug.mL-1	PMID[474653]

☑ 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 NPC322021 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	337
0.1-0.2	1227
0.2-0.3	3425
0.3-0.4	7868
0.4-0.5	10544
0.5-0.6	3970
0.6-0.7	8130
0.7-0.8	6567
0.8-0.85	512
0.85-0.9	110
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9323	High Similarity	NPC239302
0.9318	High Similarity	NPC172673
0.9155	High Similarity	NPC98009
0.9103	High Similarity	NPC327225
0.903	High Similarity	NPC195292
0.903	High Similarity	NPC142985
0.9	High Similarity	NPC476840
0.9	High Similarity	NPC476842
0.8993	High Similarity	NPC288452
0.8993	High Similarity	NPC474784
0.8993	High Similarity	NPC289690
0.8978	High Similarity	NPC139519
0.8971	High Similarity	NPC327410
0.8963	High Similarity	NPC469480
0.8921	High Similarity	NPC325625
0.8873	High Similarity	NPC46161
0.8873	High Similarity	NPC239608
0.8819	High Similarity	NPC299090
0.8819	High Similarity	NPC221383
0.8819	High Similarity	NPC143892
0.8819	High Similarity	NPC283081
0.8815	High Similarity	NPC304622
0.8806	High Similarity	NPC123722
0.8806	High Similarity	NPC123228
0.8806	High Similarity	NPC12022
0.8806	High Similarity	NPC20287
0.8806	High Similarity	NPC293641
0.8806	High Similarity	NPC151167
0.8806	High Similarity	NPC276466
0.8806	High Similarity	NPC20404
0.8806	High Similarity	NPC5018
0.8788	High Similarity	NPC257976
0.8788	High Similarity	NPC242372
0.8788	High Similarity	NPC164778
0.8788	High Similarity	NPC4181
0.875	High Similarity	NPC123196
0.875	High Similarity	NPC244246
0.875	High Similarity	NPC311419
0.875	High Similarity	NPC65935
0.875	High Similarity	NPC98356
0.875	High Similarity	NPC215941
0.875	High Similarity	NPC319282
0.875	High Similarity	NPC137427
0.875	High Similarity	NPC275724
0.8741	High Similarity	NPC278308
0.8732	High Similarity	NPC477278
0.8732	High Similarity	NPC477277
0.8731	High Similarity	NPC179777
0.8731	High Similarity	NPC84076
0.8731	High Similarity	NPC303680
0.8731	High Similarity	NPC90128
0.8723	High Similarity	NPC147379
0.8722	High Similarity	NPC312404
0.8722	High Similarity	NPC273686
0.8712	High Similarity	NPC114298
0.8705	High Similarity	NPC470990
0.8696	High Similarity	NPC129889
0.8696	High Similarity	NPC307006
0.869	High Similarity	NPC30720
0.8681	High Similarity	NPC476843
0.8681	High Similarity	NPC258671
0.8681	High Similarity	NPC469683
0.8681	High Similarity	NPC53884
0.8681	High Similarity	NPC476841
0.8662	High Similarity	NPC100675
0.8662	High Similarity	NPC78987
0.8662	High Similarity	NPC82336
0.8662	High Similarity	NPC477279
0.8657	High Similarity	NPC53305
0.8657	High Similarity	NPC257589
0.8652	High Similarity	NPC284409
0.8649	High Similarity	NPC246566
0.8649	High Similarity	NPC95498
0.8647	High Similarity	NPC163083
0.8643	High Similarity	NPC90431
0.8636	High Similarity	NPC201777
0.8633	High Similarity	NPC37065
0.8633	High Similarity	NPC471110
0.863	High Similarity	NPC1580
0.8621	High Similarity	NPC474799
0.8621	High Similarity	NPC287495
0.8621	High Similarity	NPC9370
0.8611	High Similarity	NPC160378
0.8611	High Similarity	NPC304956
0.8611	High Similarity	NPC469615
0.8601	High Similarity	NPC31751
0.8601	High Similarity	NPC253481
0.8601	High Similarity	NPC253722
0.8593	High Similarity	NPC92207
0.8593	High Similarity	NPC127937
0.8591	High Similarity	NPC44730
0.8581	High Similarity	NPC178048
0.8571	High Similarity	NPC286573
0.8571	High Similarity	NPC113295
0.8571	High Similarity	NPC474903
0.8571	High Similarity	NPC152209
0.8562	High Similarity	NPC476359
0.8562	High Similarity	NPC476338
0.8561	High Similarity	NPC168799
0.8561	High Similarity	NPC158949
0.8561	High Similarity	NPC155209
0.8552	High Similarity	NPC474982
0.8551	High Similarity	NPC198388
0.8533	High Similarity	NPC25127
0.8533	High Similarity	NPC477299
0.8529	High Similarity	NPC165045
0.8529	High Similarity	NPC118533
0.8519	High Similarity	NPC148627
0.8514	High Similarity	NPC12854
0.8511	High Similarity	NPC71638
0.8511	High Similarity	NPC64230
0.8507	High Similarity	NPC471693
0.8507	High Similarity	NPC244876
0.8503	High Similarity	NPC472969
0.85	High Similarity	NPC119060
0.85	High Similarity	NPC237594
0.85	High Similarity	NPC135127
0.85	High Similarity	NPC249791
0.85	High Similarity	NPC476387
0.8497	Intermediate Similarity	NPC472962
0.8497	Intermediate Similarity	NPC472961
0.8496	Intermediate Similarity	NPC476343
0.8493	Intermediate Similarity	NPC30890
0.8489	Intermediate Similarity	NPC50763
0.8489	Intermediate Similarity	NPC61
0.8489	Intermediate Similarity	NPC18074
0.8489	Intermediate Similarity	NPC25581
0.8489	Intermediate Similarity	NPC5419
0.8487	Intermediate Similarity	NPC476340
0.8483	Intermediate Similarity	NPC16353
0.8483	Intermediate Similarity	NPC50954
0.8483	Intermediate Similarity	NPC473090
0.8478	Intermediate Similarity	NPC339621
0.8478	Intermediate Similarity	NPC280399
0.8478	Intermediate Similarity	NPC233961
0.8467	Intermediate Similarity	NPC226661
0.8462	Intermediate Similarity	NPC470855
0.8456	Intermediate Similarity	NPC276014
0.8456	Intermediate Similarity	NPC300329
0.8446	Intermediate Similarity	NPC476394
0.8446	Intermediate Similarity	NPC98809
0.8446	Intermediate Similarity	NPC478242
0.8431	Intermediate Similarity	NPC477410
0.8429	Intermediate Similarity	NPC159418
0.8429	Intermediate Similarity	NPC475468
0.8429	Intermediate Similarity	NPC283823
0.8425	Intermediate Similarity	NPC207732
0.8425	Intermediate Similarity	NPC223185
0.8421	Intermediate Similarity	NPC473275
0.8421	Intermediate Similarity	NPC470896
0.8414	Intermediate Similarity	NPC474966
0.8411	Intermediate Similarity	NPC287504
0.8409	Intermediate Similarity	NPC320987
0.8409	Intermediate Similarity	NPC299406
0.8409	Intermediate Similarity	NPC181969
0.8403	Intermediate Similarity	NPC470991
0.8403	Intermediate Similarity	NPC51681
0.84	Intermediate Similarity	NPC93498
0.84	Intermediate Similarity	NPC476434
0.84	Intermediate Similarity	NPC163883
0.84	Intermediate Similarity	NPC151425
0.8394	Intermediate Similarity	NPC32163
0.8394	Intermediate Similarity	NPC5428
0.8394	Intermediate Similarity	NPC16651
0.8389	Intermediate Similarity	NPC177830
0.8389	Intermediate Similarity	NPC205054
0.8389	Intermediate Similarity	NPC259576
0.8389	Intermediate Similarity	NPC221091
0.8382	Intermediate Similarity	NPC280767
0.8378	Intermediate Similarity	NPC294972
0.8377	Intermediate Similarity	NPC44507
0.837	Intermediate Similarity	NPC160900
0.837	Intermediate Similarity	NPC18984
0.837	Intermediate Similarity	NPC106659
0.837	Intermediate Similarity	NPC229084
0.8369	Intermediate Similarity	NPC5310
0.8369	Intermediate Similarity	NPC68779
0.8369	Intermediate Similarity	NPC300776
0.8369	Intermediate Similarity	NPC176814
0.8369	Intermediate Similarity	NPC4982
0.8367	Intermediate Similarity	NPC472560
0.8366	Intermediate Similarity	NPC40920
0.8366	Intermediate Similarity	NPC223335
0.8358	Intermediate Similarity	NPC470804
0.8357	Intermediate Similarity	NPC111888
0.8357	Intermediate Similarity	NPC153453
0.8356	Intermediate Similarity	NPC224884
0.8356	Intermediate Similarity	NPC209085
0.8355	Intermediate Similarity	NPC300757
0.8355	Intermediate Similarity	NPC38699
0.8355	Intermediate Similarity	NPC180901
0.8355	Intermediate Similarity	NPC268008
0.8346	Intermediate Similarity	NPC177475
0.8346	Intermediate Similarity	NPC148615
0.8346	Intermediate Similarity	NPC35071
0.8345	Intermediate Similarity	NPC242807
0.8345	Intermediate Similarity	NPC187998
0.8345	Intermediate Similarity	NPC77040
0.8345	Intermediate Similarity	NPC64201
0.8345	Intermediate Similarity	NPC66905

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 NPC322021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	832
0.2-0.3	1711
0.3-0.4	2572
0.4-0.5	1965
0.5-0.6	1034
0.6-0.7	637
0.7-0.8	101
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.837	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD3027	Phase 3
0.8182	Intermediate Similarity	NPD3882	Suspended
0.8163	Intermediate Similarity	NPD6190	Approved
0.8129	Intermediate Similarity	NPD9494	Approved
0.7987	Intermediate Similarity	NPD1934	Approved
0.7937	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6166	Phase 2
0.7852	Intermediate Similarity	NPD5536	Phase 2
0.7821	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2801	Approved
0.7803	Intermediate Similarity	NPD228	Approved
0.7733	Intermediate Similarity	NPD4628	Phase 3
0.773	Intermediate Similarity	NPD3818	Discontinued
0.7722	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6355	Discontinued
0.7671	Intermediate Similarity	NPD230	Phase 1
0.7658	Intermediate Similarity	NPD3817	Phase 2
0.7643	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD8166	Discontinued
0.7605	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1613	Approved
0.7603	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1512	Approved
0.759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6797	Phase 2
0.7586	Intermediate Similarity	NPD6798	Discontinued
0.7556	Intermediate Similarity	NPD5283	Phase 1
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7534	Intermediate Similarity	NPD6233	Phase 2
0.7533	Intermediate Similarity	NPD7266	Discontinued
0.753	Intermediate Similarity	NPD7074	Phase 3
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD4966	Approved
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7483	Intermediate Similarity	NPD3620	Phase 2
0.7483	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7054	Approved
0.7468	Intermediate Similarity	NPD1511	Approved
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.744	Intermediate Similarity	NPD7685	Pre-registration
0.7438	Intermediate Similarity	NPD5402	Approved
0.7426	Intermediate Similarity	NPD1241	Discontinued
0.7425	Intermediate Similarity	NPD7472	Approved
0.7423	Intermediate Similarity	NPD8127	Discontinued
0.7415	Intermediate Similarity	NPD4062	Phase 3
0.741	Intermediate Similarity	NPD7228	Approved
0.7389	Intermediate Similarity	NPD1653	Approved
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5494	Approved
0.7355	Intermediate Similarity	NPD6799	Approved
0.7351	Intermediate Similarity	NPD2935	Discontinued
0.7349	Intermediate Similarity	NPD7473	Discontinued
0.7341	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD447	Suspended
0.7312	Intermediate Similarity	NPD6801	Discontinued
0.7308	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3751	Discontinued
0.7296	Intermediate Similarity	NPD7028	Phase 2
0.7285	Intermediate Similarity	NPD1510	Phase 2
0.7279	Intermediate Similarity	NPD7095	Approved
0.7273	Intermediate Similarity	NPD6232	Discontinued
0.7262	Intermediate Similarity	NPD5844	Phase 1
0.726	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3022	Approved
0.7259	Intermediate Similarity	NPD3021	Approved
0.7255	Intermediate Similarity	NPD2424	Discontinued
0.7251	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6386	Approved
0.725	Intermediate Similarity	NPD6385	Approved
0.7248	Intermediate Similarity	NPD943	Approved
0.7248	Intermediate Similarity	NPD1240	Approved
0.7244	Intermediate Similarity	NPD4357	Discontinued
0.7239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1357	Approved
0.7229	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5403	Approved
0.7212	Intermediate Similarity	NPD1247	Approved
0.7208	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3705	Approved
0.7197	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3146	Approved
0.7192	Intermediate Similarity	NPD5647	Approved
0.719	Intermediate Similarity	NPD5762	Approved
0.719	Intermediate Similarity	NPD5763	Approved
0.7188	Intermediate Similarity	NPD6599	Discontinued
0.7185	Intermediate Similarity	NPD2684	Approved
0.7171	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9545	Approved
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1465	Phase 2
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD6653	Approved
0.7152	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD5958	Discontinued
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD4534	Discontinued
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7125	Intermediate Similarity	NPD3455	Phase 2
0.7117	Intermediate Similarity	NPD5353	Approved
0.7113	Intermediate Similarity	NPD1651	Approved
0.7108	Intermediate Similarity	NPD7199	Phase 2
0.7101	Intermediate Similarity	NPD7843	Approved
0.7101	Intermediate Similarity	NPD2163	Approved
0.7097	Intermediate Similarity	NPD3060	Approved
0.7091	Intermediate Similarity	NPD919	Approved
0.7089	Intermediate Similarity	NPD5401	Approved
0.7086	Intermediate Similarity	NPD4340	Discontinued
0.7078	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7157	Approved
0.7066	Intermediate Similarity	NPD3787	Discontinued
0.7063	Intermediate Similarity	NPD3687	Approved
0.7063	Intermediate Similarity	NPD3686	Approved
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7055	Intermediate Similarity	NPD1876	Approved
0.7055	Intermediate Similarity	NPD1283	Approved
0.7051	Intermediate Similarity	NPD3750	Approved
0.7035	Intermediate Similarity	NPD7038	Approved
0.7035	Intermediate Similarity	NPD7039	Approved
0.7035	Intermediate Similarity	NPD6559	Discontinued
0.7034	Intermediate Similarity	NPD9269	Phase 2
0.7034	Intermediate Similarity	NPD3972	Approved
0.7032	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.7024	Intermediate Similarity	NPD3926	Phase 2
0.702	Intermediate Similarity	NPD1558	Phase 1
0.7019	Intermediate Similarity	NPD824	Approved
0.7013	Intermediate Similarity	NPD2796	Approved
0.7006	Intermediate Similarity	NPD3887	Approved
0.7006	Intermediate Similarity	NPD2354	Approved
0.7	Intermediate Similarity	NPD3764	Approved
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4236	Phase 3
0.6987	Remote Similarity	NPD4237	Approved
0.6986	Remote Similarity	NPD2982	Phase 2
0.6986	Remote Similarity	NPD2983	Phase 2
0.6985	Remote Similarity	NPD1358	Approved
0.6981	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6002	Phase 3
0.6968	Remote Similarity	NPD6004	Phase 3
0.6968	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6005	Phase 3
0.6966	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2798	Approved
0.6954	Remote Similarity	NPD2674	Phase 3
0.6944	Remote Similarity	NPD2932	Approved
0.6944	Remote Similarity	NPD17	Approved
0.6944	Remote Similarity	NPD4626	Approved
0.6939	Remote Similarity	NPD8651	Approved
0.6937	Remote Similarity	NPD6273	Approved
0.6936	Remote Similarity	NPD7240	Approved
0.6933	Remote Similarity	NPD5090	Approved
0.6933	Remote Similarity	NPD5089	Approved
0.6923	Remote Similarity	NPD5242	Approved
0.6918	Remote Similarity	NPD2981	Phase 2
0.6914	Remote Similarity	NPD7458	Discontinued
0.6914	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3018	Phase 2
0.6912	Remote Similarity	NPD3134	Approved
0.691	Remote Similarity	NPD2490	Approved
0.691	Remote Similarity	NPD2488	Approved
0.6909	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD825	Approved
0.6908	Remote Similarity	NPD826	Approved
0.6908	Remote Similarity	NPD2979	Phase 3
0.6903	Remote Similarity	NPD2438	Suspended
0.6903	Remote Similarity	NPD6099	Approved
0.6903	Remote Similarity	NPD6100	Approved
0.6897	Remote Similarity	NPD3496	Discontinued
0.6897	Remote Similarity	NPD3847	Discontinued
0.6892	Remote Similarity	NPD2797	Approved
0.6887	Remote Similarity	NPD3145	Approved
0.6887	Remote Similarity	NPD3144	Approved
0.6887	Remote Similarity	NPD3268	Approved
0.6884	Remote Similarity	NPD2067	Discontinued
0.6883	Remote Similarity	NPD7097	Phase 1
0.6879	Remote Similarity	NPD2629	Approved
0.6879	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6674	Discontinued
0.6875	Remote Similarity	NPD2534	Approved
0.6875	Remote Similarity	NPD2533	Approved
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2532	Approved
0.6871	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4908	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data