NPASS Compound

Structure

CID237424 OpenBabel06191716032D 36 40 0 0 1 0 0 0 0 0999 V2000 -2.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9898 -2.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7044 -3.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1977 -3.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4965 -4.2346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4836 -1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0388 -2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4546 -4.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8958 -1.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0768 -0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 1 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 -1.0827 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6625 -5.5218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3025 -2.9022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6646 0.5430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 36 1 0 0 0 0 2 6 1 0 0 0 0 2 15 2 0 0 0 0 3 7 2 0 0 0 0 3 15 1 0 0 0 0 4 8 1 0 0 0 0 4 16 2 0 0 0 0 5 9 2 0 0 0 0 5 16 1 0 0 0 0 6 18 2 0 0 0 0 7 18 1 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 21 2 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 14 24 2 0 0 0 0 16 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 24 27 1 0 0 0 0 24 35 1 0 0 0 0 25 15 1 6 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 26 17 1 1 0 0 0 26 27 1 0 0 0 0 28 29 1 1 0 0 0 29 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.17
Volume:	497.252
LogP:	4.12
LogD:	3.363
LogS:	-4.068
# Rotatable Bonds:	5
TPSA:	130.61
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	4.081
Fsp3:	0.172
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.877
MDCK Permeability:	5.8024425015901215e-06
Pgp-inhibitor:	0.66
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.779
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	96.3773193359375%
Volume Distribution (VD):	0.623
Pgp-substrate:	3.592176675796509%

ADMET: Metabolism

CYP1A2-inhibitor:	0.201
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.622
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.821
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.638
CYP2D6-substrate:	0.692
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	10.088
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.267
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.549
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.957
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.898
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC237424

Natural Product ID:	NPC237424
*Common Name:**	Caragasinin A
IUPAC Name:	(1R,2S,3R)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-1-[(R)-(4-hydroxyphenyl)-methoxymethyl]-2,3-dihydro-1H-indene-4,6-diol
Synonyms:	Caragasinin A
Standard InCHIKey:	XPDHVQUZVFHQNW-DZXSPZCNSA-N
Standard InCHI:	InChI=1S/C29H26O7/c1-36-29(16-4-8-19(31)9-5-16)28-23-13-22(34)14-24(35)27(23)26(17-10-20(32)12-21(33)11-17)25(28)15-2-6-18(30)7-3-15/h2-14,25-26,28-35H,1H3/t25-,26-,28-,29-/m0/s1
SMILES:	CO[C@H]([C@H]1c2cc(O)cc(c2[C@H]([C@@H]1c1ccc(cc1)O)c1cc(O)cc(c1)O)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939064
PubChem CID:	56950653
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209460]
NPO28914	Caragana sinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	66700.0	nM	PMID[501237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34700.0	nM	PMID[501237]

☑ 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 NPC237424 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	396
0.1-0.2	1608
0.2-0.3	3415
0.3-0.4	11099
0.4-0.5	8282
0.5-0.6	4866
0.6-0.7	9626
0.7-0.8	2966
0.8-0.85	315
0.85-0.9	102
0.9-0.95	12
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC238168
0.9274	High Similarity	NPC120172
0.9219	High Similarity	NPC471519
0.9219	High Similarity	NPC471518
0.9127	High Similarity	NPC97578
0.9091	High Similarity	NPC11727
0.9091	High Similarity	NPC15109
0.9077	High Similarity	NPC473309
0.9	High Similarity	NPC254000
0.8984	High Similarity	NPC9292
0.8984	High Similarity	NPC145659
0.8906	High Similarity	NPC113495
0.8832	High Similarity	NPC277784
0.8824	High Similarity	NPC174787
0.8824	High Similarity	NPC182509
0.8824	High Similarity	NPC213607
0.8806	High Similarity	NPC125579
0.8788	High Similarity	NPC471517
0.8788	High Similarity	NPC282508
0.8741	High Similarity	NPC141717
0.8667	High Similarity	NPC258780
0.8667	High Similarity	NPC37410
0.8662	High Similarity	NPC148516
0.8662	High Similarity	NPC177172
0.8662	High Similarity	NPC107862
0.8662	High Similarity	NPC122980
0.8662	High Similarity	NPC180605
0.8633	High Similarity	NPC163508
0.8633	High Similarity	NPC173203
0.8603	High Similarity	NPC133463
0.8603	High Similarity	NPC170328
0.8603	High Similarity	NPC472647
0.8603	High Similarity	NPC191462
0.8603	High Similarity	NPC472649
0.8603	High Similarity	NPC206525
0.8603	High Similarity	NPC472648
0.8601	High Similarity	NPC218801
0.8593	High Similarity	NPC473107
0.8593	High Similarity	NPC476615
0.8593	High Similarity	NPC476617
0.8593	High Similarity	NPC476616
0.8583	High Similarity	NPC69006
0.8571	High Similarity	NPC15659
0.8571	High Similarity	NPC304894
0.8561	High Similarity	NPC311293
0.8561	High Similarity	NPC148366
0.855	High Similarity	NPC170485
0.8542	High Similarity	NPC233886
0.8542	High Similarity	NPC157081
0.8542	High Similarity	NPC105073
0.8542	High Similarity	NPC224528
0.854	High Similarity	NPC71465
0.854	High Similarity	NPC472646
0.8529	High Similarity	NPC472370
0.8519	High Similarity	NPC469610
0.8519	High Similarity	NPC473665
0.8516	High Similarity	NPC102639
0.8511	High Similarity	NPC149633
0.8507	High Similarity	NPC8899
0.8483	Intermediate Similarity	NPC120633
0.8483	Intermediate Similarity	NPC473018
0.8467	Intermediate Similarity	NPC471522
0.8451	Intermediate Similarity	NPC176804
0.8451	Intermediate Similarity	NPC71686
0.8444	Intermediate Similarity	NPC469611
0.8438	Intermediate Similarity	NPC3239
0.8438	Intermediate Similarity	NPC282255
0.8421	Intermediate Similarity	NPC215300
0.8417	Intermediate Similarity	NPC472090
0.8417	Intermediate Similarity	NPC472092
0.8417	Intermediate Similarity	NPC472091
0.8417	Intermediate Similarity	NPC273623
0.8406	Intermediate Similarity	NPC94994
0.8406	Intermediate Similarity	NPC470307
0.8406	Intermediate Similarity	NPC470308
0.8397	Intermediate Similarity	NPC228503
0.8397	Intermediate Similarity	NPC138248
0.8392	Intermediate Similarity	NPC237546
0.8392	Intermediate Similarity	NPC231712
0.8392	Intermediate Similarity	NPC224921
0.8392	Intermediate Similarity	NPC112819
0.8392	Intermediate Similarity	NPC133209
0.8392	Intermediate Similarity	NPC111134
0.8392	Intermediate Similarity	NPC242774
0.8392	Intermediate Similarity	NPC6702
0.8385	Intermediate Similarity	NPC255026
0.8385	Intermediate Similarity	NPC174977
0.8382	Intermediate Similarity	NPC185777
0.8357	Intermediate Similarity	NPC472089
0.8346	Intermediate Similarity	NPC53781
0.8346	Intermediate Similarity	NPC473221
0.8333	Intermediate Similarity	NPC329836
0.8333	Intermediate Similarity	NPC105718
0.8333	Intermediate Similarity	NPC105031
0.8333	Intermediate Similarity	NPC278955
0.8308	Intermediate Similarity	NPC476633
0.8298	Intermediate Similarity	NPC183709
0.8298	Intermediate Similarity	NPC472088
0.8298	Intermediate Similarity	NPC472087
0.8286	Intermediate Similarity	NPC22317
0.8284	Intermediate Similarity	NPC47283
0.8284	Intermediate Similarity	NPC38017
0.8284	Intermediate Similarity	NPC39064
0.8271	Intermediate Similarity	NPC50315
0.8271	Intermediate Similarity	NPC230479
0.8271	Intermediate Similarity	NPC26879
0.8271	Intermediate Similarity	NPC283049
0.8271	Intermediate Similarity	NPC82299
0.8268	Intermediate Similarity	NPC261973
0.8261	Intermediate Similarity	NPC313081
0.8254	Intermediate Similarity	NPC107240
0.824	Intermediate Similarity	NPC473521
0.8239	Intermediate Similarity	NPC469630
0.8235	Intermediate Similarity	NPC472590
0.8235	Intermediate Similarity	NPC118114
0.8235	Intermediate Similarity	NPC12875
0.8235	Intermediate Similarity	NPC228369
0.8235	Intermediate Similarity	NPC129106
0.8235	Intermediate Similarity	NPC196765
0.8235	Intermediate Similarity	NPC476166
0.8235	Intermediate Similarity	NPC17343
0.8235	Intermediate Similarity	NPC206224
0.8235	Intermediate Similarity	NPC164574
0.8235	Intermediate Similarity	NPC129784
0.8235	Intermediate Similarity	NPC150011
0.8235	Intermediate Similarity	NPC280653
0.8235	Intermediate Similarity	NPC236014
0.8235	Intermediate Similarity	NPC300875
0.8235	Intermediate Similarity	NPC268917
0.8235	Intermediate Similarity	NPC207892
0.8217	Intermediate Similarity	NPC121866
0.8214	Intermediate Similarity	NPC55947
0.8214	Intermediate Similarity	NPC184613
0.8214	Intermediate Similarity	NPC20210
0.8207	Intermediate Similarity	NPC52161
0.8207	Intermediate Similarity	NPC162751
0.8203	Intermediate Similarity	NPC33270
0.8203	Intermediate Similarity	NPC69261
0.8203	Intermediate Similarity	NPC474933
0.8203	Intermediate Similarity	NPC476266
0.8201	Intermediate Similarity	NPC234952
0.8195	Intermediate Similarity	NPC476653
0.8194	Intermediate Similarity	NPC215678
0.8194	Intermediate Similarity	NPC14468
0.8194	Intermediate Similarity	NPC211758
0.8194	Intermediate Similarity	NPC87794
0.8194	Intermediate Similarity	NPC274454
0.8189	Intermediate Similarity	NPC246760
0.8189	Intermediate Similarity	NPC84999
0.8188	Intermediate Similarity	NPC296915
0.8188	Intermediate Similarity	NPC225696
0.8188	Intermediate Similarity	NPC198154
0.8188	Intermediate Similarity	NPC97834
0.8188	Intermediate Similarity	NPC223008
0.8188	Intermediate Similarity	NPC115335
0.8182	Intermediate Similarity	NPC76465
0.8182	Intermediate Similarity	NPC38761
0.8175	Intermediate Similarity	NPC13005
0.8175	Intermediate Similarity	NPC176730
0.8175	Intermediate Similarity	NPC123175
0.8162	Intermediate Similarity	NPC470225
0.8162	Intermediate Similarity	NPC126836
0.8162	Intermediate Similarity	NPC27187
0.8151	Intermediate Similarity	NPC290695
0.8151	Intermediate Similarity	NPC106524
0.8148	Intermediate Similarity	NPC53986
0.8148	Intermediate Similarity	NPC471064
0.8148	Intermediate Similarity	NPC38664
0.8143	Intermediate Similarity	NPC266006
0.8138	Intermediate Similarity	NPC153182
0.8138	Intermediate Similarity	NPC174251
0.8134	Intermediate Similarity	NPC471215
0.8134	Intermediate Similarity	NPC262573
0.8129	Intermediate Similarity	NPC69029
0.8129	Intermediate Similarity	NPC10314
0.8129	Intermediate Similarity	NPC200557
0.8129	Intermediate Similarity	NPC108198
0.8129	Intermediate Similarity	NPC294884
0.8129	Intermediate Similarity	NPC158142
0.8125	Intermediate Similarity	NPC54507
0.8125	Intermediate Similarity	NPC203113
0.8125	Intermediate Similarity	NPC141090
0.8125	Intermediate Similarity	NPC150624
0.8125	Intermediate Similarity	NPC229147
0.8125	Intermediate Similarity	NPC85292
0.8121	Intermediate Similarity	NPC473365
0.8112	Intermediate Similarity	NPC274721
0.8112	Intermediate Similarity	NPC135767
0.8112	Intermediate Similarity	NPC155392
0.8112	Intermediate Similarity	NPC184607
0.8108	Intermediate Similarity	NPC233467
0.8106	Intermediate Similarity	NPC36016
0.8106	Intermediate Similarity	NPC18128
0.8106	Intermediate Similarity	NPC100099
0.8106	Intermediate Similarity	NPC57199
0.8106	Intermediate Similarity	NPC77789
0.8102	Intermediate Similarity	NPC162801
0.8102	Intermediate Similarity	NPC181497
0.8102	Intermediate Similarity	NPC15543
0.8102	Intermediate Similarity	NPC244888

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 NPC237424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	965
0.2-0.3	1428
0.3-0.4	2882
0.4-0.5	1870
0.5-0.6	1100
0.6-0.7	518
0.7-0.8	59
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8561	High Similarity	NPD4908	Phase 1
0.8433	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD2861	Phase 2
0.803	Intermediate Similarity	NPD1610	Phase 2
0.7863	Intermediate Similarity	NPD3091	Approved
0.7826	Intermediate Similarity	NPD4625	Phase 3
0.7826	Intermediate Similarity	NPD3027	Phase 3
0.7794	Intermediate Similarity	NPD3094	Phase 2
0.7761	Intermediate Similarity	NPD3092	Approved
0.7727	Intermediate Similarity	NPD1548	Phase 1
0.7717	Intermediate Similarity	NPD4750	Phase 3
0.7671	Intermediate Similarity	NPD3892	Phase 2
0.766	Intermediate Similarity	NPD1613	Approved
0.766	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4749	Approved
0.7647	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD3095	Discontinued
0.7609	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7741	Discontinued
0.7581	Intermediate Similarity	NPD846	Approved
0.7581	Intermediate Similarity	NPD940	Approved
0.7518	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1242	Phase 1
0.7482	Intermediate Similarity	NPD4624	Approved
0.7481	Intermediate Similarity	NPD4059	Approved
0.7468	Intermediate Similarity	NPD7199	Phase 2
0.7429	Intermediate Similarity	NPD5736	Approved
0.7429	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3020	Approved
0.7413	Intermediate Similarity	NPD3620	Phase 2
0.7413	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7041	Phase 2
0.74	Intermediate Similarity	NPD7213	Phase 3
0.74	Intermediate Similarity	NPD7212	Phase 2
0.7391	Intermediate Similarity	NPD5327	Phase 3
0.7375	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5735	Approved
0.7358	Intermediate Similarity	NPD6959	Discontinued
0.7355	Intermediate Similarity	NPD37	Approved
0.7353	Intermediate Similarity	NPD3019	Approved
0.7351	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7447	Phase 1
0.731	Intermediate Similarity	NPD4097	Suspended
0.731	Intermediate Similarity	NPD6353	Approved
0.7308	Intermediate Similarity	NPD3021	Approved
0.7308	Intermediate Similarity	NPD3022	Approved
0.7292	Intermediate Similarity	NPD4060	Phase 1
0.7292	Intermediate Similarity	NPD4140	Approved
0.7287	Intermediate Similarity	NPD2342	Discontinued
0.7286	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7390	Discontinued
0.7261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6234	Discontinued
0.723	Intermediate Similarity	NPD5763	Approved
0.723	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD2932	Approved
0.7222	Intermediate Similarity	NPD6663	Approved
0.7215	Intermediate Similarity	NPD4965	Approved
0.7215	Intermediate Similarity	NPD7768	Phase 2
0.7215	Intermediate Similarity	NPD4966	Approved
0.7215	Intermediate Similarity	NPD4967	Phase 2
0.72	Intermediate Similarity	NPD3750	Approved
0.72	Intermediate Similarity	NPD7466	Approved
0.7183	Intermediate Similarity	NPD3018	Phase 2
0.7181	Intermediate Similarity	NPD7037	Approved
0.7177	Intermediate Similarity	NPD2860	Approved
0.7177	Intermediate Similarity	NPD2859	Approved
0.7172	Intermediate Similarity	NPD2238	Phase 2
0.7162	Intermediate Similarity	NPD6099	Approved
0.7162	Intermediate Similarity	NPD5405	Approved
0.7162	Intermediate Similarity	NPD5406	Approved
0.7162	Intermediate Similarity	NPD6100	Approved
0.7162	Intermediate Similarity	NPD5404	Approved
0.7162	Intermediate Similarity	NPD5408	Approved
0.7153	Intermediate Similarity	NPD3764	Approved
0.7153	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7635	Approved
0.7123	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5124	Phase 1
0.7113	Intermediate Similarity	NPD6584	Phase 3
0.7099	Intermediate Similarity	NPD7229	Phase 3
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7095	Intermediate Similarity	NPD1510	Phase 2
0.709	Intermediate Similarity	NPD5283	Phase 1
0.7067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7228	Approved
0.7029	Intermediate Similarity	NPD4093	Discontinued
0.7021	Intermediate Similarity	NPD2982	Phase 2
0.7021	Intermediate Similarity	NPD2983	Phase 2
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD422	Phase 1
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6232	Discontinued
0.6988	Remote Similarity	NPD5844	Phase 1
0.6984	Remote Similarity	NPD288	Approved
0.6981	Remote Similarity	NPD7819	Suspended
0.6981	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4626	Approved
0.697	Remote Similarity	NPD7473	Discontinued
0.6968	Remote Similarity	NPD6273	Approved
0.6963	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2157	Approved
0.6957	Remote Similarity	NPD3749	Approved
0.6954	Remote Similarity	NPD1549	Phase 2
0.695	Remote Similarity	NPD2981	Phase 2
0.6939	Remote Similarity	NPD1240	Approved
0.6929	Remote Similarity	NPD3023	Approved
0.6929	Remote Similarity	NPD3026	Approved
0.6918	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5451	Approved
0.6913	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6166	Phase 2
0.6909	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6674	Discontinued
0.6906	Remote Similarity	NPD3024	Approved
0.6906	Remote Similarity	NPD3025	Approved
0.6905	Remote Similarity	NPD844	Approved
0.6903	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6582	Phase 2
0.6901	Remote Similarity	NPD6583	Phase 3
0.6899	Remote Similarity	NPD4380	Phase 2
0.6892	Remote Similarity	NPD3657	Discovery
0.6892	Remote Similarity	NPD6355	Discontinued
0.6887	Remote Similarity	NPD7266	Discontinued
0.6867	Remote Similarity	NPD7033	Discontinued
0.6867	Remote Similarity	NPD7743	Approved
0.6867	Remote Similarity	NPD3748	Approved
0.6867	Remote Similarity	NPD7742	Approved
0.6863	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7003	Approved
0.6861	Remote Similarity	NPD6671	Approved
0.6857	Remote Similarity	NPD5125	Phase 3
0.6857	Remote Similarity	NPD5126	Approved
0.6857	Remote Similarity	NPD2286	Discontinued
0.6857	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7411	Suspended
0.6853	Remote Similarity	NPD6696	Suspended
0.6846	Remote Similarity	NPD2568	Approved
0.6846	Remote Similarity	NPD1607	Approved
0.6842	Remote Similarity	NPD8054	Approved
0.6842	Remote Similarity	NPD8053	Approved
0.6835	Remote Similarity	NPD4005	Discontinued
0.6835	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2232	Approved
0.6831	Remote Similarity	NPD2233	Approved
0.6831	Remote Similarity	NPD2230	Approved
0.6825	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2796	Approved
0.6803	Remote Similarity	NPD6798	Discontinued
0.6795	Remote Similarity	NPD2532	Approved
0.6795	Remote Similarity	NPD2534	Approved
0.6795	Remote Similarity	NPD2533	Approved
0.6795	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5691	Approved
0.6761	Remote Similarity	NPD3705	Approved
0.6761	Remote Similarity	NPD1201	Approved
0.6757	Remote Similarity	NPD6405	Approved
0.6757	Remote Similarity	NPD6407	Approved
0.6755	Remote Similarity	NPD4108	Discontinued
0.6753	Remote Similarity	NPD8166	Discontinued
0.675	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7833	Phase 2
0.6748	Remote Similarity	NPD7831	Phase 2
0.6748	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD845	Approved
0.6739	Remote Similarity	NPD709	Approved
0.6736	Remote Similarity	NPD1876	Approved
0.6736	Remote Similarity	NPD8651	Approved
0.6736	Remote Similarity	NPD1283	Approved
0.6727	Remote Similarity	NPD8127	Discontinued
0.6725	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2935	Discontinued
0.6706	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD228	Approved
0.669	Remote Similarity	NPD2797	Approved
0.669	Remote Similarity	NPD1470	Approved
0.6688	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3638	Discontinued
0.6687	Remote Similarity	NPD3787	Discontinued
0.6687	Remote Similarity	NPD3882	Suspended
0.6686	Remote Similarity	NPD8156	Discontinued
0.6667	Remote Similarity	NPD6746	Phase 2
0.6667	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD6002	Phase 3

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