NPASS Compound

Structure

CID213608 OpenBabel06191716002D 29 32 0 0 0 0 0 0 0 0999 V2000 2.5165 4.4971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7578 4.4976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6799 3.3267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2742 2.8091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6368 2.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0288 1.6872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5159 2.4665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6765 0.9681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 -1.9359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5151 -1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6774 0.9674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3534 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6768 -1.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6370 3.9897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3277 2.6077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5157 1.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8384 -1.4522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6767 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6772 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8383 -1.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5149 -0.4834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3537 0.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5152 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8382 -0.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8385 -0.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3808 0.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2331 1.4745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5150 -1.4528 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 21 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 22 2 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 28 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 25 2 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.18
Volume:	418.163
LogP:	6.991
LogD:	4.779
LogS:	-4.317
# Rotatable Bonds:	4
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.505
Synthetic Accessibility Score:	3.159
Fsp3:	0.28
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:	-4.906
MDCK Permeability:	1.599334973434452e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.119
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.697

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	90.18500518798828%
Volume Distribution (VD):	2.566
Pgp-substrate:	9.952669143676758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.756
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.88
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.601
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.322
CYP2D6-substrate:	0.707
CYP3A4-inhibitor:	0.21
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	16.182
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.539
Rat Oral Acute Toxicity:	0.677
Maximum Recommended Daily Dose:	0.235
Skin Sensitization:	0.365
Carcinogencity:	0.084
Eye Corrosion:	0.003
Eye Irritation:	0.395
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: NPC213608

Natural Product ID:	NPC213608
*Common Name:**	Erycrystagallin
IUPAC Name:	2,10-bis(3-methylbut-2-enyl)-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
Synonyms:	Erycrystagallin
Standard InCHIKey:	VNTSSLCFFUCTNP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O4/c1-14(2)5-7-16-11-19-23(12-22(16)27)28-13-20-17-9-10-21(26)18(8-6-15(3)4)24(17)29-25(19)20/h5-6,9-12,26-27H,7-8,13H2,1-4H3
SMILES:	CC(=CCc1cc2c(cc1O)OCc1c2oc2c1ccc(c2CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462699
PubChem CID:	10362969
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	root barks	n.a.	n.a.	PMID[15689169]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22444	Ceramium boydenii	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27459	Balanophora tobiracola	Species	Balanophoraceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	IC50	=	3000.0	nM	PMID[453482]

☑ 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 NPC213608 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	383
0.1-0.2	1555
0.2-0.3	3602
0.3-0.4	9532
0.4-0.5	9109
0.5-0.6	3674
0.6-0.7	5643
0.7-0.8	4909
0.8-0.85	2227
0.85-0.9	1551
0.9-0.95	468
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC1477
0.9932	High Similarity	NPC5871
0.9799	High Similarity	NPC65504
0.9733	High Similarity	NPC40583
0.9726	High Similarity	NPC226644
0.9726	High Similarity	NPC37226
0.9658	High Similarity	NPC135325
0.96	High Similarity	NPC247677
0.96	High Similarity	NPC160015
0.9597	High Similarity	NPC122365
0.9595	High Similarity	NPC170169
0.9592	High Similarity	NPC39929
0.9592	High Similarity	NPC296030
0.9589	High Similarity	NPC130581
0.9589	High Similarity	NPC12148
0.9539	High Similarity	NPC115432
0.9539	High Similarity	NPC260296
0.9536	High Similarity	NPC296957
0.9536	High Similarity	NPC260902
0.9533	High Similarity	NPC198490
0.9533	High Similarity	NPC148938
0.9527	High Similarity	NPC78335
0.9527	High Similarity	NPC230713
0.9524	High Similarity	NPC39195
0.9521	High Similarity	NPC300267
0.9521	High Similarity	NPC51641
0.9521	High Similarity	NPC210826
0.9474	High Similarity	NPC476350
0.9474	High Similarity	NPC244750
0.9474	High Similarity	NPC476349
0.9467	High Similarity	NPC472462
0.9467	High Similarity	NPC183874
0.9467	High Similarity	NPC235333
0.9459	High Similarity	NPC37208
0.9459	High Similarity	NPC221868
0.9459	High Similarity	NPC178202
0.9459	High Similarity	NPC317492
0.9456	High Similarity	NPC308200
0.9452	High Similarity	NPC230943
0.9408	High Similarity	NPC96342
0.9408	High Similarity	NPC246647
0.9408	High Similarity	NPC164110
0.9408	High Similarity	NPC268360
0.9408	High Similarity	NPC212967
0.9404	High Similarity	NPC213936
0.9404	High Similarity	NPC297531
0.94	High Similarity	NPC263676
0.94	High Similarity	NPC67654
0.94	High Similarity	NPC207624
0.9392	High Similarity	NPC168085
0.9392	High Similarity	NPC145467
0.9392	High Similarity	NPC272194
0.9388	High Similarity	NPC299011
0.9384	High Similarity	NPC225884
0.9384	High Similarity	NPC302181
0.9359	High Similarity	NPC277480
0.9355	High Similarity	NPC155640
0.9355	High Similarity	NPC472581
0.9355	High Similarity	NPC38591
0.9355	High Similarity	NPC109180
0.9351	High Similarity	NPC45124
0.9351	High Similarity	NPC30655
0.9351	High Similarity	NPC74854
0.9342	High Similarity	NPC180924
0.9333	High Similarity	NPC115324
0.9333	High Similarity	NPC193976
0.9333	High Similarity	NPC23668
0.9333	High Similarity	NPC106372
0.9333	High Similarity	NPC156244
0.9333	High Similarity	NPC116604
0.9333	High Similarity	NPC58668
0.9329	High Similarity	NPC471114
0.9324	High Similarity	NPC17816
0.932	High Similarity	NPC311144
0.932	High Similarity	NPC184649
0.932	High Similarity	NPC303185
0.932	High Similarity	NPC271288
0.9315	High Similarity	NPC53192
0.9299	High Similarity	NPC476459
0.9295	High Similarity	NPC37183
0.929	High Similarity	NPC219861
0.9276	High Similarity	NPC99199
0.9272	High Similarity	NPC473996
0.9272	High Similarity	NPC142308
0.9267	High Similarity	NPC321896
0.9267	High Similarity	NPC476185
0.9267	High Similarity	NPC29777
0.9267	High Similarity	NPC167576
0.9267	High Similarity	NPC471115
0.9257	High Similarity	NPC477955
0.9257	High Similarity	NPC472629
0.9252	High Similarity	NPC257097
0.9252	High Similarity	NPC150408
0.9252	High Similarity	NPC113770
0.9252	High Similarity	NPC106985
0.9252	High Similarity	NPC18585
0.9252	High Similarity	NPC68104
0.9252	High Similarity	NPC164980
0.9252	High Similarity	NPC91560
0.9252	High Similarity	NPC75049
0.9252	High Similarity	NPC166138
0.9252	High Similarity	NPC221432
0.9252	High Similarity	NPC169591
0.9252	High Similarity	NPC39329
0.9252	High Similarity	NPC175504
0.9252	High Similarity	NPC149026
0.9252	High Similarity	NPC310130
0.9252	High Similarity	NPC143896
0.9247	High Similarity	NPC3188
0.9211	High Similarity	NPC72370
0.9205	High Similarity	NPC472636
0.9205	High Similarity	NPC472580
0.92	High Similarity	NPC266499
0.9195	High Similarity	NPC10990
0.9195	High Similarity	NPC300988
0.9189	High Similarity	NPC311741
0.9189	High Similarity	NPC98926
0.9189	High Similarity	NPC209040
0.9189	High Similarity	NPC236766
0.9189	High Similarity	NPC473015
0.9189	High Similarity	NPC234629
0.9189	High Similarity	NPC155144
0.9189	High Similarity	NPC470890
0.9189	High Similarity	NPC473013
0.9189	High Similarity	NPC87486
0.9189	High Similarity	NPC197252
0.9189	High Similarity	NPC124780
0.9184	High Similarity	NPC144499
0.9184	High Similarity	NPC32739
0.9184	High Similarity	NPC227579
0.9184	High Similarity	NPC64915
0.9184	High Similarity	NPC223500
0.9184	High Similarity	NPC328164
0.9184	High Similarity	NPC10937
0.9184	High Similarity	NPC220998
0.9184	High Similarity	NPC194432
0.9184	High Similarity	NPC66515
0.9184	High Similarity	NPC296917
0.9184	High Similarity	NPC306829
0.9184	High Similarity	NPC324134
0.9184	High Similarity	NPC324436
0.9184	High Similarity	NPC40833
0.9184	High Similarity	NPC202981
0.9184	High Similarity	NPC76372
0.9184	High Similarity	NPC125855
0.9184	High Similarity	NPC161506
0.9184	High Similarity	NPC107572
0.9184	High Similarity	NPC182852
0.9184	High Similarity	NPC37496
0.9184	High Similarity	NPC78
0.9184	High Similarity	NPC166934
0.9184	High Similarity	NPC166482
0.9184	High Similarity	NPC148757
0.9184	High Similarity	NPC76338
0.9184	High Similarity	NPC177354
0.9184	High Similarity	NPC1089
0.9184	High Similarity	NPC265040
0.9184	High Similarity	NPC228504
0.9184	High Similarity	NPC167624
0.9182	High Similarity	NPC131866
0.9182	High Similarity	NPC120220
0.9178	High Similarity	NPC69769
0.9177	High Similarity	NPC320789
0.9167	High Similarity	NPC193998
0.9161	High Similarity	NPC304839
0.9161	High Similarity	NPC220582
0.9156	High Similarity	NPC196448
0.9145	High Similarity	NPC253872
0.9145	High Similarity	NPC327269
0.9145	High Similarity	NPC41326
0.9145	High Similarity	NPC210597
0.9145	High Similarity	NPC476238
0.9145	High Similarity	NPC31627
0.9145	High Similarity	NPC477957
0.9139	High Similarity	NPC135303
0.9139	High Similarity	NPC472406
0.9139	High Similarity	NPC148423
0.9139	High Similarity	NPC472421
0.9133	High Similarity	NPC266572
0.9133	High Similarity	NPC186397
0.9133	High Similarity	NPC37135
0.9128	High Similarity	NPC290133
0.9128	High Similarity	NPC187282
0.9128	High Similarity	NPC24136
0.9128	High Similarity	NPC473078
0.9128	High Similarity	NPC109183
0.9128	High Similarity	NPC470133
0.9128	High Similarity	NPC470134
0.9128	High Similarity	NPC470132
0.9128	High Similarity	NPC470131
0.9125	High Similarity	NPC472584
0.9122	High Similarity	NPC223812
0.9122	High Similarity	NPC85162
0.9122	High Similarity	NPC278249
0.9122	High Similarity	NPC214166
0.9122	High Similarity	NPC478086
0.9122	High Similarity	NPC77794
0.9122	High Similarity	NPC107177
0.9122	High Similarity	NPC185276
0.9122	High Similarity	NPC17262

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 NPC213608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	951
0.2-0.3	1420
0.3-0.4	2578
0.4-0.5	2014
0.5-0.6	1212
0.6-0.7	418
0.7-0.8	142
0.8-0.85	46
0.85-0.9	27
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD4378	Clinical (unspecified phase)
0.8912	High Similarity	NPD1549	Phase 2
0.891	High Similarity	NPD3749	Approved
0.8903	High Similarity	NPD8443	Clinical (unspecified phase)
0.8844	High Similarity	NPD1552	Clinical (unspecified phase)
0.8844	High Similarity	NPD1550	Clinical (unspecified phase)
0.8839	High Similarity	NPD2393	Clinical (unspecified phase)
0.8831	High Similarity	NPD7411	Suspended
0.8808	High Similarity	NPD7410	Clinical (unspecified phase)
0.8766	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD7819	Suspended
0.8716	High Similarity	NPD2344	Approved
0.8707	High Similarity	NPD1510	Phase 2
0.8696	High Similarity	NPD7852	Clinical (unspecified phase)
0.8693	High Similarity	NPD920	Approved
0.8671	High Similarity	NPD7075	Discontinued
0.8649	High Similarity	NPD2796	Approved
0.8625	High Similarity	NPD6959	Discontinued
0.8608	High Similarity	NPD7768	Phase 2
0.8606	High Similarity	NPD6559	Discontinued
0.86	High Similarity	NPD2800	Approved
0.8599	High Similarity	NPD7096	Clinical (unspecified phase)
0.8562	High Similarity	NPD5494	Approved
0.8562	High Similarity	NPD642	Clinical (unspecified phase)
0.8562	High Similarity	NPD1240	Approved
0.8535	High Similarity	NPD1934	Approved
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8487	Intermediate Similarity	NPD2309	Approved
0.8477	Intermediate Similarity	NPD1243	Approved
0.8446	Intermediate Similarity	NPD1607	Approved
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD2801	Approved
0.8355	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD2533	Approved
0.8323	Intermediate Similarity	NPD2534	Approved
0.8323	Intermediate Similarity	NPD2532	Approved
0.8302	Intermediate Similarity	NPD6801	Discontinued
0.8258	Intermediate Similarity	NPD1511	Approved
0.8258	Intermediate Similarity	NPD6799	Approved
0.8253	Intermediate Similarity	NPD3818	Discontinued
0.8242	Intermediate Similarity	NPD6166	Phase 2
0.8242	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.8204	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8171	Intermediate Similarity	NPD1247	Approved
0.8153	Intermediate Similarity	NPD1512	Approved
0.8148	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8092	Intermediate Similarity	NPD2799	Discontinued
0.8054	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD919	Approved
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8039	Intermediate Similarity	NPD1551	Phase 2
0.8	Intermediate Similarity	NPD5953	Discontinued
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7941	Intermediate Similarity	NPD7074	Phase 3
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2313	Discontinued
0.7919	Intermediate Similarity	NPD4908	Phase 1
0.7888	Intermediate Similarity	NPD3226	Approved
0.7882	Intermediate Similarity	NPD7054	Approved
0.7871	Intermediate Similarity	NPD2346	Discontinued
0.7866	Intermediate Similarity	NPD2296	Approved
0.7857	Intermediate Similarity	NPD3748	Approved
0.7857	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6651	Approved
0.7841	Intermediate Similarity	NPD4287	Approved
0.7836	Intermediate Similarity	NPD7472	Approved
0.7834	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7390	Discontinued
0.7798	Intermediate Similarity	NPD5711	Approved
0.7798	Intermediate Similarity	NPD5710	Approved
0.7798	Intermediate Similarity	NPD7229	Phase 3
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7764	Intermediate Similarity	NPD5403	Approved
0.7758	Intermediate Similarity	NPD5402	Approved
0.7746	Intermediate Similarity	NPD7251	Discontinued
0.7744	Intermediate Similarity	NPD6280	Approved
0.7744	Intermediate Similarity	NPD6279	Approved
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7701	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.7688	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1610	Phase 2
0.7667	Intermediate Similarity	NPD4360	Phase 2
0.7667	Intermediate Similarity	NPD4363	Phase 3
0.7643	Intermediate Similarity	NPD1471	Phase 3
0.764	Intermediate Similarity	NPD5401	Approved
0.764	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1729	Discontinued
0.7624	Intermediate Similarity	NPD4361	Phase 2
0.7624	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1203	Approved
0.7597	Intermediate Similarity	NPD943	Approved
0.759	Intermediate Similarity	NPD5761	Phase 2
0.759	Intermediate Similarity	NPD5760	Phase 2
0.7588	Intermediate Similarity	NPD6808	Phase 2
0.7582	Intermediate Similarity	NPD3764	Approved
0.7576	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6832	Phase 2
0.7561	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2798	Approved
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8434	Phase 2
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD4625	Phase 3
0.7468	Intermediate Similarity	NPD3268	Approved
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8312	Approved
0.7458	Intermediate Similarity	NPD8313	Approved
0.7438	Intermediate Similarity	NPD2654	Approved
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.74	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7003	Approved
0.7368	Intermediate Similarity	NPD2797	Approved
0.7358	Intermediate Similarity	NPD5408	Approved
0.7358	Intermediate Similarity	NPD5404	Approved
0.7358	Intermediate Similarity	NPD5406	Approved
0.7358	Intermediate Similarity	NPD5405	Approved
0.7349	Intermediate Similarity	NPD7458	Discontinued
0.7348	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5124	Phase 1
0.7325	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7299	Intermediate Similarity	NPD2403	Approved
0.7299	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.7285	Intermediate Similarity	NPD3972	Approved
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7278	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.7267	Intermediate Similarity	NPD2424	Discontinued
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1164	Approved
0.7255	Intermediate Similarity	NPD1470	Approved
0.7247	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7235	Intermediate Similarity	NPD4288	Approved
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7584	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD6844	Discontinued
0.7219	Intermediate Similarity	NPD37	Approved
0.7216	Intermediate Similarity	NPD7177	Discontinued
0.7215	Intermediate Similarity	NPD447	Suspended
0.7215	Intermediate Similarity	NPD1933	Approved
0.7209	Intermediate Similarity	NPD6234	Discontinued
0.7205	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6005	Phase 3
0.7205	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6002	Phase 3
0.7205	Intermediate Similarity	NPD6004	Phase 3
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.7193	Intermediate Similarity	NPD4965	Approved
0.7188	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD9545	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7171	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5889	Approved
0.716	Intermediate Similarity	NPD5890	Approved
0.7159	Intermediate Similarity	NPD3446	Phase 1
0.7151	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7134	Intermediate Similarity	NPD6798	Discontinued
0.7134	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4749	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