NPASS Compound

Structure

NPC472688 OpenBabel07101719132D 36 37 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 -3.0000 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 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 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 2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -0.5000 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 1.7321 -3.0000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 6 20 2 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 18 2 0 0 0 0 12 16 1 0 0 0 0 12 19 2 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 31 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 21 26 1 0 0 0 0 22 20 1 1 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 27 1 0 0 0 0 24 28 2 0 0 0 0 25 26 1 0 0 0 0 25 27 2 0 0 0 0 25 29 1 0 0 0 0 26 32 2 0 0 0 0 27 33 1 0 0 0 0 28 31 1 0 0 0 0 28 34 1 0 0 0 0 29 31 1 0 0 0 0 29 35 2 0 0 0 0 30 9 1 6 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.33
Volume:	553.115
LogP:	6.105
LogD:	1.627
LogS:	-2.909
# Rotatable Bonds:	9
TPSA:	88.51
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	5.06
Fsp3:	0.677
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.693
MDCK Permeability:	1.603281998541206e-05
Pgp-inhibitor:	0.308
Pgp-substrate:	0.139
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	91.28170013427734%
Volume Distribution (VD):	1.962
Pgp-substrate:	4.557582855224609%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.384
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.675

ADMET: Excretion

Clearance (CL):	10.417
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.727
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	1.0
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.051
Carcinogencity:	0.161
Eye Corrosion:	0.944
Eye Irritation:	0.117
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: NPC472688

Natural Product ID:	NPC472688
*Common Name:**	LVXMXPFAKOESBU-HBGBDTIESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LVXMXPFAKOESBU-HBGBDTIESA-N
Standard InCHI:	InChI=1S/C31H46O5/c1-10-21(8)26(32)25-27(33)24(23-17-22(20(6)7)13-14-30(23,9)36)28(34)31(29(25)35,15-11-18(2)3)16-12-19(4)5/h11-12,21-23,33-34,36H,6,10,13-17H2,1-5,7-9H3/t21?,22-,23+,30+/m0/s1
SMILES:	CCC(C(=O)C1=C(O)C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)[C@H]1C[C@H](CC[C@@]1(C)O)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581591
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001401] Menthane monoterpenoids

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO16831	Hypericum patulum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31999455]
NPO16831	Hypericum patulum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16831	Hypericum patulum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16831	Hypericum patulum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	6

Activity Type	# Activity
Cell Line	5
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[572614]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[572614]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[572614]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[572614]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[572614]
NPT23747	SINGLE PROTEIN	T-type calcium channel alpha 1G subunit	Mus musculus	IC50	=	190.0	nM	PMID[572615]

☑ 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 NPC472688 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	191
0.1-0.2	1167
0.2-0.3	4315
0.3-0.4	9459
0.4-0.5	14748
0.5-0.6	8141
0.6-0.7	4035
0.7-0.8	608
0.8-0.85	24
0.85-0.9	4
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472676
0.8588	High Similarity	NPC44963
0.8588	High Similarity	NPC472684
0.8372	Intermediate Similarity	NPC189237
0.8333	Intermediate Similarity	NPC72397
0.8242	Intermediate Similarity	NPC118011
0.8242	Intermediate Similarity	NPC36668
0.8235	Intermediate Similarity	NPC471409
0.8235	Intermediate Similarity	NPC275494
0.8222	Intermediate Similarity	NPC476079
0.8222	Intermediate Similarity	NPC113370
0.8222	Intermediate Similarity	NPC103743
0.8182	Intermediate Similarity	NPC85529
0.8182	Intermediate Similarity	NPC32006
0.8161	Intermediate Similarity	NPC226068
0.8152	Intermediate Similarity	NPC253177
0.8152	Intermediate Similarity	NPC213636
0.8152	Intermediate Similarity	NPC280592
0.8132	Intermediate Similarity	NPC472677
0.8132	Intermediate Similarity	NPC58532
0.8118	Intermediate Similarity	NPC257666
0.8118	Intermediate Similarity	NPC266193
0.8111	Intermediate Similarity	NPC470955
0.8065	Intermediate Similarity	NPC73457
0.8065	Intermediate Similarity	NPC471329
0.8065	Intermediate Similarity	NPC296114
0.8043	Intermediate Similarity	NPC472983
0.8043	Intermediate Similarity	NPC474918
0.8023	Intermediate Similarity	NPC207772
0.802	Intermediate Similarity	NPC168883
0.8	Intermediate Similarity	NPC7629
0.8	Intermediate Similarity	NPC472305
0.8	Intermediate Similarity	NPC151622
0.8	Intermediate Similarity	NPC307112
0.7957	Intermediate Similarity	NPC134321
0.7955	Intermediate Similarity	NPC275766
0.7941	Intermediate Similarity	NPC300026
0.7935	Intermediate Similarity	NPC58271
0.7935	Intermediate Similarity	NPC48107
0.7931	Intermediate Similarity	NPC170394
0.7912	Intermediate Similarity	NPC472974
0.7912	Intermediate Similarity	NPC239685
0.7907	Intermediate Similarity	NPC34110
0.7895	Intermediate Similarity	NPC474690
0.7895	Intermediate Similarity	NPC472976
0.7895	Intermediate Similarity	NPC299100
0.7895	Intermediate Similarity	NPC472977
0.7895	Intermediate Similarity	NPC196227
0.7889	Intermediate Similarity	NPC476412
0.7889	Intermediate Similarity	NPC251170
0.7872	Intermediate Similarity	NPC116726
0.7872	Intermediate Similarity	NPC472978
0.7865	Intermediate Similarity	NPC92226
0.7849	Intermediate Similarity	NPC472973
0.7849	Intermediate Similarity	NPC65615
0.7849	Intermediate Similarity	NPC68148
0.7835	Intermediate Similarity	NPC472689
0.7835	Intermediate Similarity	NPC474785
0.7835	Intermediate Similarity	NPC477268
0.7835	Intermediate Similarity	NPC477267
0.7835	Intermediate Similarity	NPC474938
0.7835	Intermediate Similarity	NPC472690
0.7831	Intermediate Similarity	NPC203819
0.7826	Intermediate Similarity	NPC471792
0.7826	Intermediate Similarity	NPC181327
0.7826	Intermediate Similarity	NPC272039
0.7826	Intermediate Similarity	NPC476409
0.7826	Intermediate Similarity	NPC220930
0.7816	Intermediate Similarity	NPC189485
0.7812	Intermediate Similarity	NPC180950
0.78	Intermediate Similarity	NPC475050
0.7778	Intermediate Similarity	NPC475083
0.7778	Intermediate Similarity	NPC282524
0.7778	Intermediate Similarity	NPC258985
0.7766	Intermediate Similarity	NPC128672
0.7766	Intermediate Similarity	NPC48010
0.7755	Intermediate Similarity	NPC471717
0.7753	Intermediate Similarity	NPC225515
0.7753	Intermediate Similarity	NPC55869
0.7753	Intermediate Similarity	NPC473217
0.7753	Intermediate Similarity	NPC121984
0.7742	Intermediate Similarity	NPC471791
0.7742	Intermediate Similarity	NPC471793
0.7738	Intermediate Similarity	NPC84790
0.7732	Intermediate Similarity	NPC472734
0.7732	Intermediate Similarity	NPC269492
0.7732	Intermediate Similarity	NPC472733
0.7732	Intermediate Similarity	NPC249954
0.7717	Intermediate Similarity	NPC194417
0.7717	Intermediate Similarity	NPC473226
0.7717	Intermediate Similarity	NPC472479
0.7708	Intermediate Similarity	NPC474882
0.7692	Intermediate Similarity	NPC40687
0.7684	Intermediate Similarity	NPC204341
0.7684	Intermediate Similarity	NPC172101
0.7677	Intermediate Similarity	NPC46761
0.766	Intermediate Similarity	NPC284561
0.766	Intermediate Similarity	NPC472970
0.766	Intermediate Similarity	NPC472971
0.7653	Intermediate Similarity	NPC170131
0.7653	Intermediate Similarity	NPC471916
0.7653	Intermediate Similarity	NPC472732
0.7653	Intermediate Similarity	NPC472731
0.7647	Intermediate Similarity	NPC247586
0.7647	Intermediate Similarity	NPC478052
0.764	Intermediate Similarity	NPC138492
0.764	Intermediate Similarity	NPC233352
0.764	Intermediate Similarity	NPC104120
0.764	Intermediate Similarity	NPC824
0.764	Intermediate Similarity	NPC306095
0.764	Intermediate Similarity	NPC2482
0.764	Intermediate Similarity	NPC148685
0.764	Intermediate Similarity	NPC108955
0.764	Intermediate Similarity	NPC476809
0.764	Intermediate Similarity	NPC157895
0.7634	Intermediate Similarity	NPC136948
0.7629	Intermediate Similarity	NPC259286
0.7629	Intermediate Similarity	NPC134067
0.7629	Intermediate Similarity	NPC777
0.7629	Intermediate Similarity	NPC280725
0.7624	Intermediate Similarity	NPC90177
0.7624	Intermediate Similarity	NPC230918
0.7624	Intermediate Similarity	NPC72151
0.7614	Intermediate Similarity	NPC478246
0.7614	Intermediate Similarity	NPC30321
0.7614	Intermediate Similarity	NPC62336
0.7614	Intermediate Similarity	NPC248624
0.7614	Intermediate Similarity	NPC179028
0.7614	Intermediate Similarity	NPC478247
0.7609	Intermediate Similarity	NPC179006
0.7609	Intermediate Similarity	NPC476426
0.7609	Intermediate Similarity	NPC255174
0.7609	Intermediate Similarity	NPC474853
0.7609	Intermediate Similarity	NPC70685
0.7609	Intermediate Similarity	NPC15807
0.7604	Intermediate Similarity	NPC474807
0.7604	Intermediate Similarity	NPC476416
0.7604	Intermediate Similarity	NPC131840
0.7604	Intermediate Similarity	NPC69454
0.7604	Intermediate Similarity	NPC472930
0.76	Intermediate Similarity	NPC470184
0.76	Intermediate Similarity	NPC472637
0.7586	Intermediate Similarity	NPC186554
0.7586	Intermediate Similarity	NPC263582
0.7586	Intermediate Similarity	NPC180886
0.7586	Intermediate Similarity	NPC76966
0.7582	Intermediate Similarity	NPC64600
0.7582	Intermediate Similarity	NPC477373
0.7582	Intermediate Similarity	NPC97913
0.7582	Intermediate Similarity	NPC49019
0.7579	Intermediate Similarity	NPC230332
0.7579	Intermediate Similarity	NPC113393
0.7576	Intermediate Similarity	NPC153776
0.7576	Intermediate Similarity	NPC472729
0.7576	Intermediate Similarity	NPC472730
0.7576	Intermediate Similarity	NPC177680
0.7576	Intermediate Similarity	NPC316598
0.7573	Intermediate Similarity	NPC473284
0.7558	Intermediate Similarity	NPC215050
0.7556	Intermediate Similarity	NPC470298
0.7556	Intermediate Similarity	NPC116797
0.7556	Intermediate Similarity	NPC6663
0.7556	Intermediate Similarity	NPC278459
0.7553	Intermediate Similarity	NPC307298
0.7551	Intermediate Similarity	NPC250757
0.7551	Intermediate Similarity	NPC21681
0.7551	Intermediate Similarity	NPC472675
0.7551	Intermediate Similarity	NPC301534
0.7549	Intermediate Similarity	NPC213366
0.7528	Intermediate Similarity	NPC281138
0.7528	Intermediate Similarity	NPC308038
0.7528	Intermediate Similarity	NPC27817
0.7527	Intermediate Similarity	NPC472869
0.7527	Intermediate Similarity	NPC472986
0.7527	Intermediate Similarity	NPC472985
0.7527	Intermediate Similarity	NPC472488
0.7527	Intermediate Similarity	NPC477478
0.7527	Intermediate Similarity	NPC477479
0.7526	Intermediate Similarity	NPC258674
0.7526	Intermediate Similarity	NPC474328
0.7526	Intermediate Similarity	NPC78159
0.7526	Intermediate Similarity	NPC8993
0.7526	Intermediate Similarity	NPC160413
0.7526	Intermediate Similarity	NPC473162
0.7525	Intermediate Similarity	NPC320447
0.7525	Intermediate Similarity	NPC473424
0.75	Intermediate Similarity	NPC61952
0.75	Intermediate Similarity	NPC266955
0.75	Intermediate Similarity	NPC154072
0.75	Intermediate Similarity	NPC97377
0.75	Intermediate Similarity	NPC473998
0.75	Intermediate Similarity	NPC74995
0.75	Intermediate Similarity	NPC164577
0.75	Intermediate Similarity	NPC472865
0.75	Intermediate Similarity	NPC132542
0.75	Intermediate Similarity	NPC472728
0.75	Intermediate Similarity	NPC63748
0.75	Intermediate Similarity	NPC472975
0.75	Intermediate Similarity	NPC473986
0.75	Intermediate Similarity	NPC472727

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 NPC472688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1466
0.2-0.3	3633
0.3-0.4	2538
0.4-0.5	901
0.5-0.6	237
0.6-0.7	179
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.764	Intermediate Similarity	NPD4695	Discontinued
0.7527	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4623	Approved
0.7527	Intermediate Similarity	NPD4519	Discontinued
0.7474	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5280	Approved
0.734	Intermediate Similarity	NPD4694	Approved
0.732	Intermediate Similarity	NPD5284	Approved
0.732	Intermediate Similarity	NPD5281	Approved
0.7292	Intermediate Similarity	NPD5328	Approved
0.7283	Intermediate Similarity	NPD4223	Phase 3
0.7283	Intermediate Similarity	NPD4221	Approved
0.7234	Intermediate Similarity	NPD5329	Approved
0.7234	Intermediate Similarity	NPD1696	Phase 3
0.7184	Intermediate Similarity	NPD5211	Phase 2
0.7158	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7129	Intermediate Similarity	NPD4755	Approved
0.7128	Intermediate Similarity	NPD4197	Approved
0.7128	Intermediate Similarity	NPD4786	Approved
0.7097	Intermediate Similarity	NPD3667	Approved
0.7071	Intermediate Similarity	NPD4202	Approved
0.7048	Intermediate Similarity	NPD5141	Approved
0.7033	Intermediate Similarity	NPD3617	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.699	Remote Similarity	NPD4700	Approved
0.699	Remote Similarity	NPD5285	Approved
0.699	Remote Similarity	NPD5286	Approved
0.699	Remote Similarity	NPD4696	Approved
0.6979	Remote Similarity	NPD4138	Approved
0.6979	Remote Similarity	NPD5279	Phase 3
0.6979	Remote Similarity	NPD4688	Approved
0.6979	Remote Similarity	NPD4693	Phase 3
0.6979	Remote Similarity	NPD5690	Phase 2
0.6979	Remote Similarity	NPD5205	Approved
0.6979	Remote Similarity	NPD4690	Approved
0.6979	Remote Similarity	NPD4689	Approved
0.6961	Remote Similarity	NPD7902	Approved
0.6947	Remote Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD3666	Approved
0.6947	Remote Similarity	NPD3665	Phase 1
0.6941	Remote Similarity	NPD7331	Phase 2
0.6939	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD5223	Approved
0.6907	Remote Similarity	NPD3573	Approved
0.69	Remote Similarity	NPD6399	Phase 3
0.69	Remote Similarity	NPD5778	Approved
0.69	Remote Similarity	NPD5779	Approved
0.6882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4096	Approved
0.6863	Remote Similarity	NPD5221	Approved
0.6863	Remote Similarity	NPD5222	Approved
0.6863	Remote Similarity	NPD4697	Phase 3
0.6863	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4633	Approved
0.6857	Remote Similarity	NPD5226	Approved
0.6857	Remote Similarity	NPD5225	Approved
0.6857	Remote Similarity	NPD5224	Approved
0.6837	Remote Similarity	NPD4518	Approved
0.6824	Remote Similarity	NPD7341	Phase 2
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6814	Remote Similarity	NPD7115	Discovery
0.68	Remote Similarity	NPD6411	Approved
0.68	Remote Similarity	NPD6050	Approved
0.6796	Remote Similarity	NPD5173	Approved
0.6792	Remote Similarity	NPD5174	Approved
0.6792	Remote Similarity	NPD4754	Approved
0.6792	Remote Similarity	NPD5175	Approved
0.6778	Remote Similarity	NPD5733	Approved
0.6774	Remote Similarity	NPD4195	Approved
0.6771	Remote Similarity	NPD3668	Phase 3
0.6737	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5133	Approved
0.6731	Remote Similarity	NPD4225	Approved
0.6727	Remote Similarity	NPD4634	Approved
0.6703	Remote Similarity	NPD8264	Approved
0.67	Remote Similarity	NPD5692	Phase 3
0.6697	Remote Similarity	NPD7320	Approved
0.6697	Remote Similarity	NPD6899	Approved
0.6697	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD6084	Phase 2
0.6635	Remote Similarity	NPD6083	Phase 2
0.6634	Remote Similarity	NPD5694	Approved
0.6606	Remote Similarity	NPD5701	Approved
0.6606	Remote Similarity	NPD5697	Approved
0.6602	Remote Similarity	NPD4629	Approved
0.6602	Remote Similarity	NPD5695	Phase 3
0.6602	Remote Similarity	NPD5210	Approved
0.66	Remote Similarity	NPD6080	Approved
0.66	Remote Similarity	NPD6101	Approved
0.66	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6673	Approved
0.66	Remote Similarity	NPD6904	Approved
0.6593	Remote Similarity	NPD4058	Approved
0.6593	Remote Similarity	NPD4687	Approved
0.6577	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD7102	Approved
0.6577	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD7638	Approved
0.6556	Remote Similarity	NPD5276	Approved
0.6545	Remote Similarity	NPD6011	Approved
0.6545	Remote Similarity	NPD4729	Approved
0.6545	Remote Similarity	NPD4730	Approved
0.6545	Remote Similarity	NPD5128	Approved
0.6538	Remote Similarity	NPD7614	Phase 1
0.6535	Remote Similarity	NPD5207	Approved
0.6526	Remote Similarity	NPD7525	Registered
0.6518	Remote Similarity	NPD6649	Approved
0.6518	Remote Similarity	NPD6869	Approved
0.6518	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6617	Approved
0.6518	Remote Similarity	NPD8130	Phase 1
0.6518	Remote Similarity	NPD6650	Approved
0.6517	Remote Similarity	NPD4137	Phase 3
0.6505	Remote Similarity	NPD5282	Discontinued
0.65	Remote Similarity	NPD6672	Approved
0.65	Remote Similarity	NPD5737	Approved
0.6495	Remote Similarity	NPD4788	Approved
0.6486	Remote Similarity	NPD6013	Approved
0.6486	Remote Similarity	NPD6014	Approved
0.6486	Remote Similarity	NPD6012	Approved
0.6471	Remote Similarity	NPD5693	Phase 1
0.6471	Remote Similarity	NPD7637	Suspended
0.6465	Remote Similarity	NPD7146	Approved
0.6465	Remote Similarity	NPD5330	Approved
0.6465	Remote Similarity	NPD7521	Approved
0.6465	Remote Similarity	NPD6684	Approved
0.6465	Remote Similarity	NPD7334	Approved
0.6465	Remote Similarity	NPD6409	Approved
0.646	Remote Similarity	NPD6882	Approved
0.646	Remote Similarity	NPD8297	Approved
0.6458	Remote Similarity	NPD4692	Approved
0.6458	Remote Similarity	NPD4139	Approved
0.6444	Remote Similarity	NPD4747	Approved
0.6444	Remote Similarity	NPD4691	Approved
0.6442	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5249	Phase 3
0.6429	Remote Similarity	NPD5135	Approved
0.6429	Remote Similarity	NPD5251	Approved
0.6429	Remote Similarity	NPD5248	Approved
0.6429	Remote Similarity	NPD5247	Approved
0.6429	Remote Similarity	NPD5169	Approved
0.6429	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5250	Approved
0.6429	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5696	Approved
0.6413	Remote Similarity	NPD4785	Approved
0.6413	Remote Similarity	NPD6926	Approved
0.6413	Remote Similarity	NPD4784	Approved
0.6413	Remote Similarity	NPD6924	Approved
0.6392	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4756	Discovery
0.6374	Remote Similarity	NPD4243	Approved
0.6373	Remote Similarity	NPD5785	Approved
0.6372	Remote Similarity	NPD5215	Approved
0.6372	Remote Similarity	NPD5217	Approved
0.6372	Remote Similarity	NPD5127	Approved
0.6372	Remote Similarity	NPD5216	Approved
0.6364	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD5363	Approved
0.6356	Remote Similarity	NPD6054	Approved
0.6356	Remote Similarity	NPD6059	Approved
0.6354	Remote Similarity	NPD6931	Approved
0.6354	Remote Similarity	NPD6930	Phase 2
0.6344	Remote Similarity	NPD7339	Approved
0.6344	Remote Similarity	NPD6942	Approved
0.6337	Remote Similarity	NPD5208	Approved
0.6337	Remote Similarity	NPD6903	Approved
0.6337	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6695	Phase 3
0.6316	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6098	Approved
0.6286	Remote Similarity	NPD5654	Approved
0.6277	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6933	Approved
0.6261	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD6929	Approved
0.625	Remote Similarity	NPD5168	Approved
0.625	Remote Similarity	NPD6370	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.6239	Remote Similarity	NPD5091	Approved
0.6238	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4269	Approved
0.6224	Remote Similarity	NPD4270	Approved
0.6218	Remote Similarity	NPD6319	Approved
0.6207	Remote Similarity	NPD5167	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