NPASS Compound

Structure

NPC472732 OpenBabel07101718292D 37 39 0 0 1 0 0 0 0 0999 V2000 -1.5218 3.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6175 -2.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1941 -2.9399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8218 -4.2702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1798 2.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 0.1284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3285 0.5402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0893 -2.3339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2963 0.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7674 2.9296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2452 -1.2963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1941 -1.2963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6436 -2.8468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6436 -1.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7707 -0.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9802 0.0809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6686 -2.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8218 -3.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0964 2.2586 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8218 -1.4234 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3033 -0.1964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4532 -0.4770 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3420 1.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6990 0.2156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3580 -0.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8218 -0.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 -0.4061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8218 -1.4234 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8218 -0.4745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2586 1.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8404 1.1539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 0.4745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9340 -1.1902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0686 -1.0993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 7 29 1 0 0 0 0 8 29 1 0 0 0 0 10 31 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 22 1 0 0 0 0 16 31 1 0 0 0 0 17 23 1 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 30 1 0 0 0 0 21 6 1 6 0 0 0 21 25 1 0 0 0 0 22 31 1 6 0 0 0 23 26 1 0 0 0 0 23 27 2 0 0 0 0 24 29 1 6 0 0 0 24 37 1 0 0 0 0 25 33 2 0 0 0 0 26 32 1 0 0 0 0 26 34 2 0 0 0 0 27 30 1 0 0 0 0 27 37 1 0 0 0 0 28 30 1 0 0 0 0 28 32 1 0 0 0 0 28 35 2 0 0 0 0 29 36 1 0 0 0 0 30 9 1 6 0 0 0 31 32 1 1 0 0 0 32 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.35
Volume:	564.491
LogP:	6.722
LogD:	5.295
LogS:	-5.152
# Rotatable Bonds:	9
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	6.024
Fsp3:	0.719
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	1.6324005628121085e-05
Pgp-inhibitor:	0.111
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.099
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.828
Plasma Protein Binding (PPB):	90.17363739013672%
Volume Distribution (VD):	2.051
Pgp-substrate:	5.178251266479492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.244
CYP2C19-inhibitor:	0.225
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.375
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	10.128
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.799
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.385
Skin Sensitization:	0.225
Carcinogencity:	0.738
Eye Corrosion:	0.019
Eye Irritation:	0.077
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC472732

Natural Product ID:	NPC472732
*Common Name:**	ANTMNBWQNGONEF-QJAHKVHPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ANTMNBWQNGONEF-QJAHKVHPSA-N
Standard InCHI:	InChI=1S/C32H48O5/c1-11-21(6)25(33)32-26(34)23-17-24(29(7,8)36)37-27(23)30(9,28(32)35)18-22(15-14-20(4)5)31(32,10)16-12-13-19(2)3/h13-14,21-22,24,36H,11-12,15-18H2,1-10H3/t21-,22-,24+,30+,31+,32-/m0/s1
SMILES:	CC[C@@H](C(=O)[C@]12C(=O)C3=C([C@@](C1=O)(C)C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)O[C@H](C3)C(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581916
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] 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
NPO32997	Hypericum monogynum	Species	Hypericaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[25924023]
NPO32997	Hypericum monogynum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27525351]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15200.0	nM	PMID[473110]

☑ 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 NPC472732 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	1228
0.2-0.3	4489
0.3-0.4	9046
0.4-0.5	13655
0.5-0.6	7559
0.6-0.7	5656
0.7-0.8	816
0.8-0.85	13
0.85-0.9	10
0.9-0.95	18
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472731
0.9889	High Similarity	NPC472733
0.9889	High Similarity	NPC472734
0.9783	High Similarity	NPC472727
0.9783	High Similarity	NPC472728
0.9674	High Similarity	NPC177680
0.9674	High Similarity	NPC472730
0.9674	High Similarity	NPC153776
0.9674	High Similarity	NPC472729
0.9462	High Similarity	NPC471331
0.9462	High Similarity	NPC472687
0.9462	High Similarity	NPC203388
0.9462	High Similarity	NPC471330
0.9462	High Similarity	NPC99657
0.9355	High Similarity	NPC27105
0.9082	High Similarity	NPC471333
0.9082	High Similarity	NPC471332
0.9043	High Similarity	NPC21681
0.9043	High Similarity	NPC472675
0.8791	High Similarity	NPC38885
0.875	High Similarity	NPC239895
0.8632	High Similarity	NPC469819
0.8632	High Similarity	NPC114162
0.8438	Intermediate Similarity	NPC477241
0.8333	Intermediate Similarity	NPC44963
0.8333	Intermediate Similarity	NPC472684
0.8265	Intermediate Similarity	NPC135576
0.8265	Intermediate Similarity	NPC93271
0.8235	Intermediate Similarity	NPC13385
0.8113	Intermediate Similarity	NPC324683
0.8056	Intermediate Similarity	NPC247069
0.8039	Intermediate Similarity	NPC473163
0.802	Intermediate Similarity	NPC46761
0.802	Intermediate Similarity	NPC54705
0.8019	Intermediate Similarity	NPC239097
0.7981	Intermediate Similarity	NPC478052
0.798	Intermediate Similarity	NPC473170
0.7961	Intermediate Similarity	NPC474207
0.7961	Intermediate Similarity	NPC474330
0.7941	Intermediate Similarity	NPC270155
0.7941	Intermediate Similarity	NPC475867
0.7938	Intermediate Similarity	NPC472325
0.7935	Intermediate Similarity	NPC189237
0.7925	Intermediate Similarity	NPC470257
0.7885	Intermediate Similarity	NPC40170
0.7879	Intermediate Similarity	NPC473172
0.7864	Intermediate Similarity	NPC163249
0.785	Intermediate Similarity	NPC473627
0.7849	Intermediate Similarity	NPC212083
0.7802	Intermediate Similarity	NPC478247
0.7802	Intermediate Similarity	NPC478246
0.7789	Intermediate Similarity	NPC79573
0.7788	Intermediate Similarity	NPC264048
0.7778	Intermediate Similarity	NPC474229
0.7778	Intermediate Similarity	NPC474807
0.7778	Intermediate Similarity	NPC61275
0.7778	Intermediate Similarity	NPC43775
0.7767	Intermediate Similarity	NPC476213
0.7767	Intermediate Similarity	NPC477871
0.7767	Intermediate Similarity	NPC101067
0.7767	Intermediate Similarity	NPC476246
0.7767	Intermediate Similarity	NPC476134
0.7767	Intermediate Similarity	NPC477870
0.7755	Intermediate Similarity	NPC469464
0.7742	Intermediate Similarity	NPC327002
0.7736	Intermediate Similarity	NPC58370
0.7736	Intermediate Similarity	NPC43285
0.7732	Intermediate Similarity	NPC143025
0.7723	Intermediate Similarity	NPC8803
0.7723	Intermediate Similarity	NPC473164
0.7714	Intermediate Similarity	NPC255309
0.7708	Intermediate Similarity	NPC470345
0.7708	Intermediate Similarity	NPC477478
0.7708	Intermediate Similarity	NPC477479
0.77	Intermediate Similarity	NPC472976
0.77	Intermediate Similarity	NPC472977
0.77	Intermediate Similarity	NPC67831
0.77	Intermediate Similarity	NPC196227
0.77	Intermediate Similarity	NPC473162
0.77	Intermediate Similarity	NPC174051
0.7692	Intermediate Similarity	NPC476235
0.7692	Intermediate Similarity	NPC473928
0.7692	Intermediate Similarity	NPC80781
0.7692	Intermediate Similarity	NPC476126
0.7692	Intermediate Similarity	NPC325946
0.7685	Intermediate Similarity	NPC37116
0.7677	Intermediate Similarity	NPC116726
0.7677	Intermediate Similarity	NPC296114
0.7677	Intermediate Similarity	NPC262870
0.7677	Intermediate Similarity	NPC19114
0.7677	Intermediate Similarity	NPC471329
0.7677	Intermediate Similarity	NPC475441
0.7677	Intermediate Similarity	NPC146852
0.767	Intermediate Similarity	NPC316964
0.767	Intermediate Similarity	NPC112167
0.7664	Intermediate Similarity	NPC473482
0.7664	Intermediate Similarity	NPC475418
0.7664	Intermediate Similarity	NPC318363
0.7653	Intermediate Similarity	NPC474570
0.7653	Intermediate Similarity	NPC472676
0.7653	Intermediate Similarity	NPC472688
0.7653	Intermediate Similarity	NPC32830
0.7653	Intermediate Similarity	NPC477943
0.7647	Intermediate Similarity	NPC53844
0.7647	Intermediate Similarity	NPC124246
0.7647	Intermediate Similarity	NPC477268
0.7647	Intermediate Similarity	NPC477267
0.7647	Intermediate Similarity	NPC473161
0.7647	Intermediate Similarity	NPC472689
0.7647	Intermediate Similarity	NPC472690
0.7642	Intermediate Similarity	NPC292588
0.7642	Intermediate Similarity	NPC102352
0.7642	Intermediate Similarity	NPC85529
0.7642	Intermediate Similarity	NPC32006
0.7642	Intermediate Similarity	NPC96377
0.7634	Intermediate Similarity	NPC2482
0.7629	Intermediate Similarity	NPC472324
0.7629	Intermediate Similarity	NPC90652
0.7627	Intermediate Similarity	NPC294050
0.7627	Intermediate Similarity	NPC328997
0.7604	Intermediate Similarity	NPC6185
0.7604	Intermediate Similarity	NPC8518
0.7604	Intermediate Similarity	NPC241512
0.7604	Intermediate Similarity	NPC263997
0.7604	Intermediate Similarity	NPC469948
0.7604	Intermediate Similarity	NPC132228
0.7596	Intermediate Similarity	NPC181645
0.7596	Intermediate Similarity	NPC473514
0.7593	Intermediate Similarity	NPC87335
0.7593	Intermediate Similarity	NPC475065
0.7593	Intermediate Similarity	NPC41405
0.7579	Intermediate Similarity	NPC64600
0.7579	Intermediate Similarity	NPC278648
0.7579	Intermediate Similarity	NPC476082
0.7576	Intermediate Similarity	NPC213636
0.7576	Intermediate Similarity	NPC166554
0.7576	Intermediate Similarity	NPC15059
0.7576	Intermediate Similarity	NPC113393
0.7576	Intermediate Similarity	NPC253177
0.7576	Intermediate Similarity	NPC280592
0.7573	Intermediate Similarity	NPC147954
0.7573	Intermediate Similarity	NPC471582
0.757	Intermediate Similarity	NPC220974
0.757	Intermediate Similarity	NPC473169
0.757	Intermediate Similarity	NPC3316
0.757	Intermediate Similarity	NPC144854
0.757	Intermediate Similarity	NPC473284
0.7553	Intermediate Similarity	NPC116797
0.7551	Intermediate Similarity	NPC53911
0.7551	Intermediate Similarity	NPC470417
0.7551	Intermediate Similarity	NPC476708
0.7549	Intermediate Similarity	NPC471775
0.7549	Intermediate Similarity	NPC471463
0.7547	Intermediate Similarity	NPC149124
0.7547	Intermediate Similarity	NPC146731
0.7547	Intermediate Similarity	NPC75531
0.7545	Intermediate Similarity	NPC269530
0.7544	Intermediate Similarity	NPC478051
0.7527	Intermediate Similarity	NPC327674
0.7526	Intermediate Similarity	NPC473168
0.7526	Intermediate Similarity	NPC145879
0.7526	Intermediate Similarity	NPC474733
0.7526	Intermediate Similarity	NPC31564
0.7526	Intermediate Similarity	NPC194417
0.7526	Intermediate Similarity	NPC474778
0.7526	Intermediate Similarity	NPC220478
0.7526	Intermediate Similarity	NPC474732
0.7525	Intermediate Similarity	NPC318332
0.7524	Intermediate Similarity	NPC478176
0.7524	Intermediate Similarity	NPC70369
0.7524	Intermediate Similarity	NPC477915
0.7524	Intermediate Similarity	NPC473424
0.7523	Intermediate Similarity	NPC29133
0.7523	Intermediate Similarity	NPC5284
0.75	Intermediate Similarity	NPC474720
0.75	Intermediate Similarity	NPC473288
0.75	Intermediate Similarity	NPC151393
0.75	Intermediate Similarity	NPC192813
0.75	Intermediate Similarity	NPC214043
0.75	Intermediate Similarity	NPC316553
0.75	Intermediate Similarity	NPC270929
0.75	Intermediate Similarity	NPC154608
0.75	Intermediate Similarity	NPC473166
0.75	Intermediate Similarity	NPC476274
0.75	Intermediate Similarity	NPC473246
0.75	Intermediate Similarity	NPC230623
0.75	Intermediate Similarity	NPC207217
0.75	Intermediate Similarity	NPC167974
0.75	Intermediate Similarity	NPC85774
0.75	Intermediate Similarity	NPC277017
0.75	Intermediate Similarity	NPC110149
0.75	Intermediate Similarity	NPC248913
0.75	Intermediate Similarity	NPC117685
0.75	Intermediate Similarity	NPC238005
0.75	Intermediate Similarity	NPC141196
0.75	Intermediate Similarity	NPC303697
0.75	Intermediate Similarity	NPC1980
0.7477	Intermediate Similarity	NPC326264
0.7477	Intermediate Similarity	NPC149047
0.7477	Intermediate Similarity	NPC198539

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 NPC472732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1585
0.2-0.3	3848
0.3-0.4	2364
0.4-0.5	724
0.5-0.6	231
0.6-0.7	212
0.7-0.8	13
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
0.7475	Intermediate Similarity	NPD5328	Approved
0.7426	Intermediate Similarity	NPD6399	Phase 3
0.7353	Intermediate Similarity	NPD7748	Approved
0.7353	Intermediate Similarity	NPD5282	Discontinued
0.7347	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3618	Phase 1
0.7327	Intermediate Similarity	NPD6079	Approved
0.732	Intermediate Similarity	NPD3665	Phase 1
0.732	Intermediate Similarity	NPD3666	Approved
0.732	Intermediate Similarity	NPD4786	Approved
0.732	Intermediate Similarity	NPD3133	Approved
0.7308	Intermediate Similarity	NPD7902	Approved
0.7292	Intermediate Similarity	NPD3667	Approved
0.7281	Intermediate Similarity	NPD7115	Discovery
0.7263	Intermediate Similarity	NPD4695	Discontinued
0.7232	Intermediate Similarity	NPD8297	Approved
0.7212	Intermediate Similarity	NPD4697	Phase 3
0.7172	Intermediate Similarity	NPD6409	Approved
0.7172	Intermediate Similarity	NPD6684	Approved
0.7172	Intermediate Similarity	NPD5330	Approved
0.7172	Intermediate Similarity	NPD7146	Approved
0.7172	Intermediate Similarity	NPD7521	Approved
0.7172	Intermediate Similarity	NPD7334	Approved
0.7157	Intermediate Similarity	NPD6411	Approved
0.7156	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD5739	Approved
0.7156	Intermediate Similarity	NPD6675	Approved
0.7156	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD4755	Approved
0.7129	Intermediate Similarity	NPD4753	Phase 2
0.7117	Intermediate Similarity	NPD6373	Approved
0.7117	Intermediate Similarity	NPD6372	Approved
0.7115	Intermediate Similarity	NPD5695	Phase 3
0.7113	Intermediate Similarity	NPD4221	Approved
0.7113	Intermediate Similarity	NPD4223	Phase 3
0.7091	Intermediate Similarity	NPD6412	Phase 2
0.7075	Intermediate Similarity	NPD5696	Approved
0.7075	Intermediate Similarity	NPD4225	Approved
0.7071	Intermediate Similarity	NPD5329	Approved
0.7054	Intermediate Similarity	NPD4634	Approved
0.7048	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5222	Approved
0.7048	Intermediate Similarity	NPD5221	Approved
0.703	Intermediate Similarity	NPD5737	Approved
0.703	Intermediate Similarity	NPD6903	Approved
0.703	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6672	Approved
0.7027	Intermediate Similarity	NPD6881	Approved
0.7027	Intermediate Similarity	NPD7320	Approved
0.7027	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD7900	Approved
0.7019	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5286	Approved
0.7009	Intermediate Similarity	NPD4700	Approved
0.7009	Intermediate Similarity	NPD4696	Approved
0.7009	Intermediate Similarity	NPD5285	Approved
0.7	Intermediate Similarity	NPD5279	Phase 3
0.6991	Remote Similarity	NPD6650	Approved
0.6991	Remote Similarity	NPD6649	Approved
0.6991	Remote Similarity	NPD8130	Phase 1
0.699	Remote Similarity	NPD7515	Phase 2
0.6981	Remote Similarity	NPD5173	Approved
0.697	Remote Similarity	NPD3668	Phase 3
0.697	Remote Similarity	NPD4197	Approved
0.6961	Remote Similarity	NPD6101	Approved
0.6961	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5210	Approved
0.6952	Remote Similarity	NPD4629	Approved
0.6949	Remote Similarity	NPD6319	Approved
0.6949	Remote Similarity	NPD6054	Approved
0.6949	Remote Similarity	NPD6059	Approved
0.6944	Remote Similarity	NPD5223	Approved
0.6939	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5701	Approved
0.6937	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD4202	Approved
0.6917	Remote Similarity	NPD8328	Phase 3
0.6903	Remote Similarity	NPD7290	Approved
0.6903	Remote Similarity	NPD7102	Approved
0.6903	Remote Similarity	NPD6883	Approved
0.6881	Remote Similarity	NPD5211	Phase 2
0.6881	Remote Similarity	NPD5225	Approved
0.6881	Remote Similarity	NPD5226	Approved
0.6881	Remote Similarity	NPD5224	Approved
0.6881	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD3617	Approved
0.6875	Remote Similarity	NPD6011	Approved
0.687	Remote Similarity	NPD4632	Approved
0.6847	Remote Similarity	NPD6008	Approved
0.6842	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6869	Approved
0.6842	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD6617	Approved
0.6833	Remote Similarity	NPD6370	Approved
0.6832	Remote Similarity	NPD4693	Phase 3
0.6832	Remote Similarity	NPD4689	Approved
0.6832	Remote Similarity	NPD4623	Approved
0.6832	Remote Similarity	NPD4138	Approved
0.6832	Remote Similarity	NPD4694	Approved
0.6832	Remote Similarity	NPD4519	Discontinued
0.6832	Remote Similarity	NPD5280	Approved
0.6832	Remote Similarity	NPD4688	Approved
0.6832	Remote Similarity	NPD5205	Approved
0.6832	Remote Similarity	NPD5690	Phase 2
0.6832	Remote Similarity	NPD4690	Approved
0.6827	Remote Similarity	NPD5281	Approved
0.6827	Remote Similarity	NPD5284	Approved
0.6818	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD5174	Approved
0.6818	Remote Similarity	NPD4754	Approved
0.6814	Remote Similarity	NPD6014	Approved
0.6814	Remote Similarity	NPD6013	Approved
0.6814	Remote Similarity	NPD6012	Approved
0.6796	Remote Similarity	NPD6080	Approved
0.6796	Remote Similarity	NPD6673	Approved
0.6796	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6904	Approved
0.6792	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6882	Approved
0.6778	Remote Similarity	NPD7331	Phase 2
0.6768	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3573	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6757	Remote Similarity	NPD5141	Approved
0.675	Remote Similarity	NPD6015	Approved
0.675	Remote Similarity	NPD6016	Approved
0.6748	Remote Similarity	NPD8293	Discontinued
0.6726	Remote Similarity	NPD6686	Approved
0.6721	Remote Similarity	NPD7492	Approved
0.67	Remote Similarity	NPD4788	Approved
0.6696	Remote Similarity	NPD4767	Approved
0.6696	Remote Similarity	NPD4768	Approved
0.6694	Remote Similarity	NPD5988	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD6050	Approved
0.6638	Remote Similarity	NPD6053	Discontinued
0.6613	Remote Similarity	NPD7078	Approved
0.6609	Remote Similarity	NPD6371	Approved
0.6579	Remote Similarity	NPD5128	Approved
0.6579	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4730	Approved
0.6579	Remote Similarity	NPD4729	Approved
0.6571	Remote Similarity	NPD5692	Phase 3
0.6571	Remote Similarity	NPD5207	Approved
0.6571	Remote Similarity	NPD5785	Approved
0.6569	Remote Similarity	NPD1694	Approved
0.6566	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6033	Approved
0.6555	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6009	Approved
0.6538	Remote Similarity	NPD5208	Approved
0.6535	Remote Similarity	NPD6110	Phase 1
0.6522	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5694	Approved
0.6509	Remote Similarity	NPD8034	Phase 2
0.6509	Remote Similarity	NPD5693	Phase 1
0.6509	Remote Similarity	NPD8035	Phase 2
0.6509	Remote Similarity	NPD7983	Approved
0.6508	Remote Similarity	NPD7319	Approved
0.6505	Remote Similarity	NPD6098	Approved
0.6505	Remote Similarity	NPD5786	Approved
0.6504	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD6335	Approved
0.6495	Remote Similarity	NPD6933	Approved
0.6491	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5983	Phase 2
0.6471	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD6868	Approved
0.6466	Remote Similarity	NPD5169	Approved
0.6466	Remote Similarity	NPD5250	Approved
0.6466	Remote Similarity	NPD5249	Phase 3
0.6466	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5248	Approved
0.6466	Remote Similarity	NPD5251	Approved
0.6466	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5247	Approved
0.6466	Remote Similarity	NPD5135	Approved
0.6465	Remote Similarity	NPD4195	Approved
0.6455	Remote Similarity	NPD7638	Approved
0.6446	Remote Similarity	NPD7101	Approved
0.6446	Remote Similarity	NPD7100	Approved
0.6442	Remote Similarity	NPD7524	Approved
0.6435	Remote Similarity	NPD5168	Approved
0.6417	Remote Similarity	NPD6317	Approved
0.6415	Remote Similarity	NPD4096	Approved
0.641	Remote Similarity	NPD5127	Approved
0.641	Remote Similarity	NPD5216	Approved
0.641	Remote Similarity	NPD5215	Approved
0.641	Remote Similarity	NPD5217	Approved
0.6408	Remote Similarity	NPD5363	Approved
0.64	Remote Similarity	NPD7507	Approved
0.64	Remote Similarity	NPD6336	Discontinued
0.6396	Remote Similarity	NPD7640	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