NPASS Compound

Structure

CID71210 OpenBabel06191715412D 22 24 0 0 1 0 0 0 0 0999 V2000 4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0574 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0574 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.9234 0.5865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 -1.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 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 21 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	772.59
Volume:	858.858
LogP:	12.991
LogD:	5.004
LogS:	-4.481
# Rotatable Bonds:	34
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.032
Synthetic Accessibility Score:	4.914
Fsp3:	0.83
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.231
MDCK Permeability:	3.76988236894249e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.483
Plasma Protein Binding (PPB):	96.84783172607422%
Volume Distribution (VD):	1.343
Pgp-substrate:	2.4379825592041016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.21
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.569
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	4.796
Half-life (T1/2):	0.0

ADMET: Toxicity

hERG Blockers:	0.765
Human Hepatotoxicity (H-HT):	0.77
Drug-inuced Liver Injury (DILI):	0.756
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.771
Skin Sensitization:	0.951
Carcinogencity:	0.005
Eye Corrosion:	0.032
Eye Irritation:	0.017
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC71210

Natural Product ID:	NPC71210
*Common Name:**	Carpusin
IUPAC Name:	2,6-dihydroxy-2-[(4-hydroxyphenyl)methyl]-4-methoxy-1-benzofuran-3-one
Synonyms:	Carasinaurone; Carpusin; Marsuosin; Marsupsin
Standard InCHIKey:	IQTGAKWQIFFPQX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-21-12-6-11(18)7-13-14(12)15(19)16(20,22-13)8-9-2-4-10(17)5-3-9/h2-7,17-18,20H,8H2,1H3
SMILES:	COc1cc(O)cc2c1C(=O)C(O2)(O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512396
PubChem CID:	134369
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001631] Aurone flavonoids [CHEMONTID:0003471] Auronols

*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
NPO20312	Pterocarpus marsupium	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	DOI[10.1021/np50031a029]
NPO20312	Pterocarpus marsupium	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	DOI[10.1021/np50031a029]
NPO30021	Rheum emodi	Species	Polygonaceae	Eukaryota	Roots	Gorkha district, Nepal	1996-OCT	PMID[12932135]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209460]
NPO20312	Pterocarpus marsupium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377021]
NPO20312	Pterocarpus marsupium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214733]
NPO30021	Rheum emodi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20312	Pterocarpus marsupium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12759	Rheum australe	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20312	Pterocarpus marsupium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12759	Rheum australe	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20312	Pterocarpus marsupium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28914	Caragana sinica	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	3
Others	9

Activity Type	# Activity
NON-MOLECULAR	1
Organism	9
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	20.0	%	PMID[494199]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	64.0	%	PMID[494199]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	33.0	%	PMID[494199]
NPT1	Others	Radical scavenging activity		IC50	=	4.7	ug.mL-1	PMID[494200]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	350.6	mg/dl	PMID[494201]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	19.05	mg/dl	PMID[494201]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	32.0	mg/dl	PMID[494201]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	292.8	mg/dl	PMID[494201]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	41.1	mg/dl	PMID[494201]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Ratio	=	0.09	n.a.	PMID[494201]
NPT1	Others	Radical scavenging activity		IC50	>	200000.0	nM	PMID[494202]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[494202]

☑ 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 NPC71210 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	353
0.1-0.2	1624
0.2-0.3	4310
0.3-0.4	10503
0.4-0.5	7613
0.5-0.6	3788
0.6-0.7	5995
0.7-0.8	5137
0.8-0.85	2378
0.85-0.9	865
0.9-0.95	128
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC310128
0.9712	High Similarity	NPC471520
0.9429	High Similarity	NPC230285
0.9429	High Similarity	NPC59951
0.9429	High Similarity	NPC103342
0.9429	High Similarity	NPC103904
0.9429	High Similarity	NPC184536
0.9429	High Similarity	NPC146679
0.9366	High Similarity	NPC470216
0.9362	High Similarity	NPC136840
0.9362	High Similarity	NPC262094
0.9362	High Similarity	NPC90582
0.9357	High Similarity	NPC152042
0.9357	High Similarity	NPC143799
0.9357	High Similarity	NPC241838
0.9353	High Similarity	NPC254841
0.9291	High Similarity	NPC281207
0.9291	High Similarity	NPC269652
0.9236	High Similarity	NPC178343
0.9236	High Similarity	NPC5820
0.9236	High Similarity	NPC306488
0.9231	High Similarity	NPC158874
0.9184	High Similarity	NPC318424
0.9178	High Similarity	NPC477941
0.9167	High Similarity	NPC273538
0.9167	High Similarity	NPC216538
0.9161	High Similarity	NPC266725
0.9161	High Similarity	NPC200694
0.9161	High Similarity	NPC473042
0.9149	High Similarity	NPC124269
0.9149	High Similarity	NPC276905
0.9143	High Similarity	NPC473887
0.9143	High Similarity	NPC194281
0.9143	High Similarity	NPC234133
0.9143	High Similarity	NPC231772
0.9143	High Similarity	NPC216361
0.9143	High Similarity	NPC127447
0.9143	High Similarity	NPC116775
0.9143	High Similarity	NPC256042
0.9143	High Similarity	NPC187432
0.9143	High Similarity	NPC281917
0.9143	High Similarity	NPC47815
0.9143	High Similarity	NPC29353
0.9143	High Similarity	NPC124784
0.9133	High Similarity	NPC210048
0.9133	High Similarity	NPC161650
0.9103	High Similarity	NPC124729
0.9103	High Similarity	NPC153758
0.9103	High Similarity	NPC470458
0.9097	High Similarity	NPC24821
0.9097	High Similarity	NPC302181
0.9097	High Similarity	NPC9117
0.9097	High Similarity	NPC293053
0.9097	High Similarity	NPC212932
0.9097	High Similarity	NPC190637
0.9085	High Similarity	NPC274784
0.9085	High Similarity	NPC310135
0.9085	High Similarity	NPC20709
0.9085	High Similarity	NPC265871
0.9085	High Similarity	NPC222342
0.9085	High Similarity	NPC78913
0.9085	High Similarity	NPC150648
0.9085	High Similarity	NPC329203
0.9085	High Similarity	NPC18260
0.9085	High Similarity	NPC225153
0.9078	High Similarity	NPC250266
0.9078	High Similarity	NPC299379
0.9078	High Similarity	NPC266597
0.9078	High Similarity	NPC188879
0.9073	High Similarity	NPC264932
0.9073	High Similarity	NPC311574
0.9065	High Similarity	NPC82225
0.9065	High Similarity	NPC18877
0.9065	High Similarity	NPC20560
0.9065	High Similarity	NPC204960
0.9065	High Similarity	NPC144051
0.9065	High Similarity	NPC294593
0.9065	High Similarity	NPC159623
0.9065	High Similarity	NPC28753
0.9054	High Similarity	NPC295650
0.9048	High Similarity	NPC470461
0.9041	High Similarity	NPC476182
0.9041	High Similarity	NPC122828
0.9041	High Similarity	NPC211466
0.9041	High Similarity	NPC176869
0.9041	High Similarity	NPC44721
0.9041	High Similarity	NPC40086
0.9041	High Similarity	NPC3779
0.9041	High Similarity	NPC472918
0.9034	High Similarity	NPC326500
0.9034	High Similarity	NPC230943
0.9028	High Similarity	NPC53192
0.9021	High Similarity	NPC110228
0.9021	High Similarity	NPC159275
0.9021	High Similarity	NPC129853
0.9021	High Similarity	NPC188243
0.9021	High Similarity	NPC6407
0.9021	High Similarity	NPC241100
0.9021	High Similarity	NPC76445
0.9021	High Similarity	NPC284550
0.9014	High Similarity	NPC118813
0.9014	High Similarity	NPC201395
0.9014	High Similarity	NPC99333
0.9014	High Similarity	NPC280284
0.9014	High Similarity	NPC188947
0.9013	High Similarity	NPC269906
0.9013	High Similarity	NPC306978
0.9013	High Similarity	NPC172687
0.9007	High Similarity	NPC288084
0.9007	High Similarity	NPC13408
0.9007	High Similarity	NPC240593
0.9007	High Similarity	NPC72452
0.9007	High Similarity	NPC240147
0.9007	High Similarity	NPC61546
0.9007	High Similarity	NPC121243
0.9	High Similarity	NPC248872
0.9	High Similarity	NPC286336
0.8993	High Similarity	NPC129132
0.8993	High Similarity	NPC257756
0.8993	High Similarity	NPC212631
0.8993	High Similarity	NPC205468
0.8993	High Similarity	NPC87231
0.898	High Similarity	NPC168085
0.898	High Similarity	NPC244407
0.898	High Similarity	NPC296869
0.898	High Similarity	NPC470460
0.8973	High Similarity	NPC229190
0.8966	High Similarity	NPC113770
0.8958	High Similarity	NPC324386
0.8958	High Similarity	NPC110969
0.8958	High Similarity	NPC213322
0.8958	High Similarity	NPC3188
0.8958	High Similarity	NPC4743
0.8958	High Similarity	NPC282300
0.8958	High Similarity	NPC312391
0.8951	High Similarity	NPC303633
0.8951	High Similarity	NPC96565
0.8951	High Similarity	NPC216978
0.8951	High Similarity	NPC261234
0.8951	High Similarity	NPC55018
0.8951	High Similarity	NPC301217
0.8951	High Similarity	NPC140890
0.8951	High Similarity	NPC220062
0.8951	High Similarity	NPC230902
0.8951	High Similarity	NPC217186
0.8951	High Similarity	NPC53181
0.8944	High Similarity	NPC295261
0.8944	High Similarity	NPC287246
0.8944	High Similarity	NPC107586
0.8944	High Similarity	NPC290291
0.8944	High Similarity	NPC296490
0.8944	High Similarity	NPC275055
0.8944	High Similarity	NPC32441
0.8944	High Similarity	NPC228661
0.8944	High Similarity	NPC243083
0.8944	High Similarity	NPC12296
0.8944	High Similarity	NPC79943
0.8944	High Similarity	NPC13768
0.894	High Similarity	NPC476652
0.894	High Similarity	NPC211482
0.8936	High Similarity	NPC239495
0.8936	High Similarity	NPC9985
0.8936	High Similarity	NPC13575
0.8929	High Similarity	NPC139813
0.8929	High Similarity	NPC337373
0.8929	High Similarity	NPC175098
0.8929	High Similarity	NPC188646
0.8929	High Similarity	NPC274121
0.8929	High Similarity	NPC242294
0.8929	High Similarity	NPC50898
0.8929	High Similarity	NPC213216
0.8929	High Similarity	NPC56031
0.8929	High Similarity	NPC192304
0.8929	High Similarity	NPC312318
0.8929	High Similarity	NPC263670
0.8929	High Similarity	NPC78540
0.8929	High Similarity	NPC472365
0.8921	High Similarity	NPC475589
0.8921	High Similarity	NPC186097
0.8921	High Similarity	NPC473584
0.8921	High Similarity	NPC308037
0.8921	High Similarity	NPC64359
0.8921	High Similarity	NPC262359
0.8921	High Similarity	NPC313618
0.8921	High Similarity	NPC475009
0.8921	High Similarity	NPC475008
0.8921	High Similarity	NPC31872
0.8919	High Similarity	NPC37226
0.8919	High Similarity	NPC226644
0.8919	High Similarity	NPC317492
0.8919	High Similarity	NPC277032
0.8912	High Similarity	NPC17816
0.8912	High Similarity	NPC12148
0.8912	High Similarity	NPC166757
0.8912	High Similarity	NPC130581
0.8912	High Similarity	NPC259632
0.8912	High Similarity	NPC14001
0.8904	High Similarity	NPC49130
0.8904	High Similarity	NPC208176
0.8904	High Similarity	NPC279417

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 NPC71210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	931
0.2-0.3	1606
0.3-0.4	2650
0.4-0.5	1881
0.5-0.6	1162
0.6-0.7	419
0.7-0.8	129
0.8-0.85	35
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD4378	Clinical (unspecified phase)
0.8944	High Similarity	NPD1550	Clinical (unspecified phase)
0.8944	High Similarity	NPD1552	Clinical (unspecified phase)
0.8921	High Similarity	NPD1240	Approved
0.8881	High Similarity	NPD1549	Phase 2
0.8836	High Similarity	NPD6799	Approved
0.8794	High Similarity	NPD1607	Approved
0.8693	High Similarity	NPD3882	Suspended
0.8671	High Similarity	NPD1510	Phase 2
0.8636	High Similarity	NPD7075	Discontinued
0.8609	High Similarity	NPD6599	Discontinued
0.8591	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD7410	Clinical (unspecified phase)
0.8516	High Similarity	NPD4381	Clinical (unspecified phase)
0.85	High Similarity	NPD7804	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD6801	Discontinued
0.8497	Intermediate Similarity	NPD1934	Approved
0.8483	Intermediate Similarity	NPD2796	Approved
0.8456	Intermediate Similarity	NPD1511	Approved
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD2800	Approved
0.8431	Intermediate Similarity	NPD7411	Suspended
0.8387	Intermediate Similarity	NPD3817	Phase 2
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD2801	Approved
0.8282	Intermediate Similarity	NPD6797	Phase 2
0.828	Intermediate Similarity	NPD3749	Approved
0.8269	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD3750	Approved
0.8252	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD4380	Phase 2
0.8243	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7251	Discontinued
0.8231	Intermediate Similarity	NPD1551	Phase 2
0.8205	Intermediate Similarity	NPD7819	Suspended
0.8199	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6166	Phase 2
0.8188	Intermediate Similarity	NPD1243	Approved
0.8182	Intermediate Similarity	NPD7808	Phase 3
0.8176	Intermediate Similarity	NPD2344	Approved
0.817	Intermediate Similarity	NPD5403	Approved
0.817	Intermediate Similarity	NPD920	Approved
0.8158	Intermediate Similarity	NPD5401	Approved
0.8133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7074	Phase 3
0.8072	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7054	Approved
0.8039	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD2534	Approved
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2532	Approved
0.8028	Intermediate Similarity	NPD1203	Approved
0.8026	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD7472	Approved
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD7768	Phase 2
0.7975	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2309	Approved
0.7925	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD3748	Approved
0.7905	Intermediate Similarity	NPD6651	Approved
0.7901	Intermediate Similarity	NPD6959	Discontinued
0.7901	Intermediate Similarity	NPD1247	Approved
0.784	Intermediate Similarity	NPD5494	Approved
0.7831	Intermediate Similarity	NPD7286	Phase 2
0.7817	Intermediate Similarity	NPD9717	Approved
0.7805	Intermediate Similarity	NPD3926	Phase 2
0.78	Intermediate Similarity	NPD2799	Discontinued
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2313	Discontinued
0.7751	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD422	Phase 1
0.7744	Intermediate Similarity	NPD6232	Discontinued
0.774	Intermediate Similarity	NPD6832	Phase 2
0.7738	Intermediate Similarity	NPD5953	Discontinued
0.7724	Intermediate Similarity	NPD2798	Approved
0.7712	Intermediate Similarity	NPD2654	Approved
0.7711	Intermediate Similarity	NPD7473	Discontinued
0.7707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD943	Approved
0.7635	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3226	Approved
0.76	Intermediate Similarity	NPD1933	Approved
0.759	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1548	Phase 1
0.7582	Intermediate Similarity	NPD1471	Phase 3
0.756	Intermediate Similarity	NPD3751	Discontinued
0.7545	Intermediate Similarity	NPD2403	Approved
0.7534	Intermediate Similarity	NPD2797	Approved
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6798	Discontinued
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD2354	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7483	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7466	Intermediate Similarity	NPD3225	Approved
0.7465	Intermediate Similarity	NPD9545	Approved
0.7451	Intermediate Similarity	NPD4308	Phase 3
0.7451	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1608	Approved
0.7447	Intermediate Similarity	NPD9493	Approved
0.743	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3787	Discontinued
0.7425	Intermediate Similarity	NPD5711	Approved
0.7425	Intermediate Similarity	NPD5710	Approved
0.7423	Intermediate Similarity	NPD1465	Phase 2
0.7415	Intermediate Similarity	NPD3266	Approved
0.7415	Intermediate Similarity	NPD3267	Approved
0.7412	Intermediate Similarity	NPD5844	Phase 1
0.7401	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1296	Phase 2
0.74	Intermediate Similarity	NPD3764	Approved
0.74	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2296	Approved
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD1729	Discontinued
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7365	Intermediate Similarity	NPD7199	Phase 2
0.7355	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2353	Approved
0.7351	Intermediate Similarity	NPD6233	Phase 2
0.7338	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1481	Phase 2
0.7329	Intermediate Similarity	NPD3972	Approved
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7390	Discontinued
0.7288	Intermediate Similarity	NPD4287	Approved
0.7285	Intermediate Similarity	NPD411	Approved
0.7278	Intermediate Similarity	NPD3887	Approved
0.7278	Intermediate Similarity	NPD4361	Phase 2
0.7278	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4288	Approved
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1535	Discovery
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD17	Approved
0.7235	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.7222	Intermediate Similarity	NPD4360	Phase 2
0.7222	Intermediate Similarity	NPD4363	Phase 3
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7205	Intermediate Similarity	NPD5049	Phase 3
0.72	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1613	Approved
0.719	Intermediate Similarity	NPD4307	Phase 2
0.7178	Intermediate Similarity	NPD7458	Discontinued
0.7175	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4966	Approved
0.7124	Intermediate Similarity	NPD4062	Phase 3
0.7119	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1876	Approved
0.7103	Intermediate Similarity	NPD1894	Discontinued
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7078	Intermediate Similarity	NPD4060	Phase 1
0.7074	Intermediate Similarity	NPD7584	Approved
0.7067	Intermediate Similarity	NPD1164	Approved
0.7052	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6280	Approved
0.7048	Intermediate Similarity	NPD6279	Approved
0.7039	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6782	Approved
0.7027	Intermediate Similarity	NPD6781	Approved
0.7027	Intermediate Similarity	NPD6780	Approved
0.7027	Intermediate Similarity	NPD6778	Approved
0.7027	Intermediate Similarity	NPD6777	Approved
0.7027	Intermediate Similarity	NPD6779	Approved
0.7027	Intermediate Similarity	NPD1201	Approved
0.7027	Intermediate Similarity	NPD6776	Approved
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6808	Phase 2
0.7006	Intermediate Similarity	NPD8313	Approved
0.7006	Intermediate Similarity	NPD8312	Approved
0.7005	Intermediate Similarity	NPD7435	Discontinued

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