NPASS Compound

Structure

NPC472730 OpenBabel07101718332D 36 38 0 0 1 0 0 0 0 0999 V2000 3.9533 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7285 2.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 1.2765 1.5397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0569 2.6451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5426 -1.6353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6416 -2.0692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8518 -1.6678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2802 0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2207 -1.5853 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 2.9873 1.6213 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 0.2906 1.7075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5075 -1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7191 -0.9973 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3476 0.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -0.5243 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 2.7163 -1.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -1.3334 1.1055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0196 -2.7160 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 3.2797 -0.2458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3139 -0.3416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 20 1 0 0 0 0 7 28 1 0 0 0 0 8 28 1 0 0 0 0 10 30 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 21 1 0 0 0 0 15 30 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 20 24 1 0 0 0 0 21 30 1 1 0 0 0 22 25 1 0 0 0 0 22 26 2 0 0 0 0 23 28 1 6 0 0 0 23 36 1 0 0 0 0 24 32 2 0 0 0 0 25 29 1 0 0 0 0 25 33 2 0 0 0 0 26 31 1 0 0 0 0 26 36 1 0 0 0 0 27 29 1 0 0 0 0 27 31 1 0 0 0 0 27 34 2 0 0 0 0 28 35 1 0 0 0 0 29 9 1 6 0 0 0 30 31 1 6 0 0 0 31 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.33
Volume:	547.195
LogP:	6.395
LogD:	5.203
LogS:	-5.166
# Rotatable Bonds:	8
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.314
Synthetic Accessibility Score:	5.906
Fsp3:	0.71
Lipinski Rule-of-5:	Accepted
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:	-5.039
MDCK Permeability:	1.7590120478416793e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.936

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.494
Plasma Protein Binding (PPB):	91.59793853759766%
Volume Distribution (VD):	1.785
Pgp-substrate:	5.262569427490234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.539
CYP2C19-inhibitor:	0.145
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.217
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	10.137
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.021
Carcinogencity:	0.797
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.728

Download Data

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

Natural Product: NPC472730

Natural Product ID:	NPC472730
*Common Name:**	WSKJZPUOPKLDDO-PBZDJEQUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WSKJZPUOPKLDDO-PBZDJEQUSA-N
Standard InCHI:	InChI=1S/C31H46O5/c1-18(2)12-11-15-30(10)21(14-13-19(3)4)17-29(9)25(33)22-16-23(28(7,8)35)36-26(22)31(30,27(29)34)24(32)20(5)6/h12-13,20-21,23,35H,11,14-17H2,1-10H3/t21-,23-,29+,30+,31-/m0/s1
SMILES:	CC(C)C(=O)C12C3=C(CC(O3)C(C)(C)O)C(=O)C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581914
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	>	50000.0	nM	PMID[460915]

☑ 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 NPC472730 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	192
0.1-0.2	1262
0.2-0.3	4588
0.3-0.4	9128
0.4-0.5	13782
0.5-0.6	7928
0.6-0.7	5069
0.7-0.8	690
0.8-0.85	17
0.85-0.9	12
0.9-0.95	13
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC153776
1.0	High Similarity	NPC472729
1.0	High Similarity	NPC177680
0.9891	High Similarity	NPC472728
0.9891	High Similarity	NPC472727
0.978	High Similarity	NPC472734
0.978	High Similarity	NPC472733
0.9674	High Similarity	NPC472731
0.9674	High Similarity	NPC472732
0.9255	High Similarity	NPC27105
0.9158	High Similarity	NPC99657
0.9158	High Similarity	NPC471331
0.9158	High Similarity	NPC471330
0.9158	High Similarity	NPC472687
0.9158	High Similarity	NPC203388
0.9149	High Similarity	NPC472675
0.9149	High Similarity	NPC21681
0.8936	High Similarity	NPC469819
0.8936	High Similarity	NPC114162
0.88	High Similarity	NPC471332
0.88	High Similarity	NPC471333
0.866	High Similarity	NPC239895
0.8495	Intermediate Similarity	NPC38885
0.8351	Intermediate Similarity	NPC477241
0.83	Intermediate Similarity	NPC46761
0.8242	Intermediate Similarity	NPC189237
0.8182	Intermediate Similarity	NPC135576
0.8182	Intermediate Similarity	NPC93271
0.8155	Intermediate Similarity	NPC13385
0.8137	Intermediate Similarity	NPC163249
0.8043	Intermediate Similarity	NPC44963
0.8043	Intermediate Similarity	NPC472684
0.8	Intermediate Similarity	NPC473164
0.7982	Intermediate Similarity	NPC247069
0.7944	Intermediate Similarity	NPC239097
0.7941	Intermediate Similarity	NPC54705
0.7921	Intermediate Similarity	NPC477268
0.7921	Intermediate Similarity	NPC473161
0.7921	Intermediate Similarity	NPC472689
0.7921	Intermediate Similarity	NPC472690
0.7921	Intermediate Similarity	NPC477267
0.7905	Intermediate Similarity	NPC85529
0.7905	Intermediate Similarity	NPC478052
0.7905	Intermediate Similarity	NPC32006
0.7905	Intermediate Similarity	NPC292588
0.79	Intermediate Similarity	NPC473170
0.7885	Intermediate Similarity	NPC474330
0.7885	Intermediate Similarity	NPC474207
0.787	Intermediate Similarity	NPC324683
0.7864	Intermediate Similarity	NPC101067
0.7864	Intermediate Similarity	NPC475867
0.7864	Intermediate Similarity	NPC477871
0.7864	Intermediate Similarity	NPC477870
0.7864	Intermediate Similarity	NPC270155
0.7864	Intermediate Similarity	NPC476213
0.7864	Intermediate Similarity	NPC476134
0.7864	Intermediate Similarity	NPC476246
0.7857	Intermediate Similarity	NPC472325
0.785	Intermediate Similarity	NPC470257
0.7843	Intermediate Similarity	NPC147954
0.781	Intermediate Similarity	NPC40170
0.78	Intermediate Similarity	NPC473172
0.78	Intermediate Similarity	NPC318332
0.7788	Intermediate Similarity	NPC476126
0.7788	Intermediate Similarity	NPC476235
0.7788	Intermediate Similarity	NPC473163
0.7767	Intermediate Similarity	NPC110149
0.7766	Intermediate Similarity	NPC212083
0.7745	Intermediate Similarity	NPC124246
0.7745	Intermediate Similarity	NPC273269
0.7732	Intermediate Similarity	NPC99909
0.7717	Intermediate Similarity	NPC478247
0.7717	Intermediate Similarity	NPC478246
0.7714	Intermediate Similarity	NPC264048
0.7714	Intermediate Similarity	NPC320294
0.7714	Intermediate Similarity	NPC239716
0.7708	Intermediate Similarity	NPC79573
0.7706	Intermediate Similarity	NPC474229
0.77	Intermediate Similarity	NPC474807
0.77	Intermediate Similarity	NPC61275
0.7677	Intermediate Similarity	NPC469464
0.7664	Intermediate Similarity	NPC43285
0.7664	Intermediate Similarity	NPC58370
0.7653	Intermediate Similarity	NPC474854
0.7653	Intermediate Similarity	NPC143025
0.7647	Intermediate Similarity	NPC8803
0.7647	Intermediate Similarity	NPC471775
0.7647	Intermediate Similarity	NPC269492
0.7642	Intermediate Similarity	NPC255309
0.7636	Intermediate Similarity	NPC205534
0.7636	Intermediate Similarity	NPC193948
0.7629	Intermediate Similarity	NPC229717
0.7629	Intermediate Similarity	NPC203795
0.7629	Intermediate Similarity	NPC470345
0.7624	Intermediate Similarity	NPC196227
0.7624	Intermediate Similarity	NPC67831
0.7624	Intermediate Similarity	NPC472977
0.7624	Intermediate Similarity	NPC473162
0.7624	Intermediate Similarity	NPC472976
0.7624	Intermediate Similarity	NPC174051
0.7619	Intermediate Similarity	NPC80781
0.7615	Intermediate Similarity	NPC473627
0.7615	Intermediate Similarity	NPC37116
0.7609	Intermediate Similarity	NPC325946
0.76	Intermediate Similarity	NPC262870
0.76	Intermediate Similarity	NPC475441
0.76	Intermediate Similarity	NPC146852
0.76	Intermediate Similarity	NPC19114
0.76	Intermediate Similarity	NPC116726
0.7596	Intermediate Similarity	NPC316964
0.7596	Intermediate Similarity	NPC198880
0.7596	Intermediate Similarity	NPC112167
0.7583	Intermediate Similarity	NPC316553
0.7576	Intermediate Similarity	NPC477943
0.7576	Intermediate Similarity	NPC32830
0.7576	Intermediate Similarity	NPC472676
0.7576	Intermediate Similarity	NPC472688
0.7573	Intermediate Similarity	NPC472073
0.7573	Intermediate Similarity	NPC53844
0.7573	Intermediate Similarity	NPC472074
0.757	Intermediate Similarity	NPC102352
0.757	Intermediate Similarity	NPC96377
0.7568	Intermediate Similarity	NPC326264
0.7565	Intermediate Similarity	NPC471999
0.7565	Intermediate Similarity	NPC472000
0.7553	Intermediate Similarity	NPC2482
0.7551	Intermediate Similarity	NPC90652
0.7551	Intermediate Similarity	NPC472324
0.7549	Intermediate Similarity	NPC31021
0.7547	Intermediate Similarity	NPC475321
0.7545	Intermediate Similarity	NPC34315
0.7545	Intermediate Similarity	NPC43775
0.7526	Intermediate Similarity	NPC132228
0.7526	Intermediate Similarity	NPC6185
0.7526	Intermediate Similarity	NPC469948
0.7526	Intermediate Similarity	NPC263997
0.7526	Intermediate Similarity	NPC241512
0.7526	Intermediate Similarity	NPC8518
0.7524	Intermediate Similarity	NPC181645
0.7524	Intermediate Similarity	NPC9878
0.7523	Intermediate Similarity	NPC87335
0.7523	Intermediate Similarity	NPC153239
0.7523	Intermediate Similarity	NPC250018
0.75	Intermediate Similarity	NPC280592
0.75	Intermediate Similarity	NPC253177
0.75	Intermediate Similarity	NPC473169
0.75	Intermediate Similarity	NPC473898
0.75	Intermediate Similarity	NPC476082
0.75	Intermediate Similarity	NPC166554
0.75	Intermediate Similarity	NPC213636
0.75	Intermediate Similarity	NPC64600
0.75	Intermediate Similarity	NPC278648
0.75	Intermediate Similarity	NPC3316
0.75	Intermediate Similarity	NPC113393
0.75	Intermediate Similarity	NPC15059
0.75	Intermediate Similarity	NPC144854
0.7478	Intermediate Similarity	NPC478051
0.7477	Intermediate Similarity	NPC269530
0.7477	Intermediate Similarity	NPC149124
0.7477	Intermediate Similarity	NPC470104
0.7477	Intermediate Similarity	NPC75531
0.7477	Intermediate Similarity	NPC146731
0.7476	Intermediate Similarity	NPC471463
0.7476	Intermediate Similarity	NPC125622
0.7475	Intermediate Similarity	NPC476708
0.7475	Intermediate Similarity	NPC53911
0.7475	Intermediate Similarity	NPC470417
0.7474	Intermediate Similarity	NPC116797
0.7474	Intermediate Similarity	NPC327002
0.7456	Intermediate Similarity	NPC106644
0.7456	Intermediate Similarity	NPC17772
0.7455	Intermediate Similarity	NPC286880
0.7455	Intermediate Similarity	NPC29133
0.7453	Intermediate Similarity	NPC477915
0.7453	Intermediate Similarity	NPC478176
0.7453	Intermediate Similarity	NPC473424
0.7453	Intermediate Similarity	NPC473928
0.7453	Intermediate Similarity	NPC70369
0.7449	Intermediate Similarity	NPC474732
0.7449	Intermediate Similarity	NPC473168
0.7449	Intermediate Similarity	NPC31564
0.7449	Intermediate Similarity	NPC474778
0.7449	Intermediate Similarity	NPC220478
0.7449	Intermediate Similarity	NPC474733
0.7449	Intermediate Similarity	NPC477479
0.7449	Intermediate Similarity	NPC194417
0.7449	Intermediate Similarity	NPC145879
0.7449	Intermediate Similarity	NPC477478
0.7447	Intermediate Similarity	NPC28319
0.7434	Intermediate Similarity	NPC270929
0.7434	Intermediate Similarity	NPC207217
0.7431	Intermediate Similarity	NPC473482
0.7431	Intermediate Similarity	NPC475418
0.7431	Intermediate Similarity	NPC154608
0.7431	Intermediate Similarity	NPC192813
0.7431	Intermediate Similarity	NPC277017
0.7431	Intermediate Similarity	NPC318363
0.7431	Intermediate Similarity	NPC151393
0.7431	Intermediate Similarity	NPC473288
0.7431	Intermediate Similarity	NPC19412

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 NPC472730 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	1619
0.2-0.3	3867
0.3-0.4	2330
0.4-0.5	729
0.5-0.6	215
0.6-0.7	206
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
0.74	Intermediate Similarity	NPD5328	Approved
0.7353	Intermediate Similarity	NPD6399	Phase 3
0.7333	Intermediate Similarity	NPD5696	Approved
0.7282	Intermediate Similarity	NPD5282	Discontinued
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7255	Intermediate Similarity	NPD6079	Approved
0.7245	Intermediate Similarity	NPD4786	Approved
0.7245	Intermediate Similarity	NPD3133	Approved
0.7245	Intermediate Similarity	NPD3665	Phase 1
0.7245	Intermediate Similarity	NPD3666	Approved
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7216	Intermediate Similarity	NPD3667	Approved
0.7212	Intermediate Similarity	NPD4629	Approved
0.7212	Intermediate Similarity	NPD5210	Approved
0.7188	Intermediate Similarity	NPD4695	Discontinued
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7115	Intermediate Similarity	NPD7748	Approved
0.71	Intermediate Similarity	NPD6684	Approved
0.71	Intermediate Similarity	NPD7334	Approved
0.71	Intermediate Similarity	NPD7146	Approved
0.71	Intermediate Similarity	NPD7521	Approved
0.71	Intermediate Similarity	NPD6409	Approved
0.71	Intermediate Similarity	NPD5330	Approved
0.7091	Intermediate Similarity	NPD6675	Approved
0.7091	Intermediate Similarity	NPD6402	Approved
0.7091	Intermediate Similarity	NPD5739	Approved
0.7091	Intermediate Similarity	NPD7128	Approved
0.7087	Intermediate Similarity	NPD6411	Approved
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD7902	Approved
0.7075	Intermediate Similarity	NPD4755	Approved
0.7059	Intermediate Similarity	NPD4753	Phase 2
0.7054	Intermediate Similarity	NPD6373	Approved
0.7054	Intermediate Similarity	NPD6372	Approved
0.7048	Intermediate Similarity	NPD5695	Phase 3
0.7041	Intermediate Similarity	NPD4223	Phase 3
0.7041	Intermediate Similarity	NPD4221	Approved
0.7027	Intermediate Similarity	NPD6412	Phase 2
0.7018	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD4225	Approved
0.7	Intermediate Similarity	NPD5329	Approved
0.6991	Remote Similarity	NPD4634	Approved
0.6981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5221	Approved
0.6981	Remote Similarity	NPD5222	Approved
0.6964	Remote Similarity	NPD7320	Approved
0.6964	Remote Similarity	NPD6899	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6672	Approved
0.6961	Remote Similarity	NPD5737	Approved
0.6961	Remote Similarity	NPD6903	Approved
0.6944	Remote Similarity	NPD4700	Approved
0.6944	Remote Similarity	NPD5285	Approved
0.6944	Remote Similarity	NPD4696	Approved
0.6944	Remote Similarity	NPD5286	Approved
0.6931	Remote Similarity	NPD5279	Phase 3
0.693	Remote Similarity	NPD6650	Approved
0.693	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD7515	Phase 2
0.6916	Remote Similarity	NPD5173	Approved
0.69	Remote Similarity	NPD4197	Approved
0.69	Remote Similarity	NPD3668	Phase 3
0.6893	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6101	Approved
0.6891	Remote Similarity	NPD6319	Approved
0.6891	Remote Similarity	NPD6059	Approved
0.6891	Remote Similarity	NPD6054	Approved
0.6881	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD5697	Approved
0.6869	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4202	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6818	Remote Similarity	NPD5211	Phase 2
0.6818	Remote Similarity	NPD5224	Approved
0.6818	Remote Similarity	NPD5225	Approved
0.6818	Remote Similarity	NPD5226	Approved
0.6818	Remote Similarity	NPD4633	Approved
0.6814	Remote Similarity	NPD6011	Approved
0.681	Remote Similarity	NPD4632	Approved
0.6804	Remote Similarity	NPD3617	Approved
0.6792	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6008	Approved
0.6783	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8130	Phase 1
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.6777	Remote Similarity	NPD6370	Approved
0.6765	Remote Similarity	NPD5280	Approved
0.6765	Remote Similarity	NPD4690	Approved
0.6765	Remote Similarity	NPD4694	Approved
0.6765	Remote Similarity	NPD4519	Discontinued
0.6765	Remote Similarity	NPD4689	Approved
0.6765	Remote Similarity	NPD4623	Approved
0.6765	Remote Similarity	NPD5205	Approved
0.6765	Remote Similarity	NPD4693	Phase 3
0.6765	Remote Similarity	NPD4138	Approved
0.6765	Remote Similarity	NPD5690	Phase 2
0.6765	Remote Similarity	NPD4688	Approved
0.6762	Remote Similarity	NPD5284	Approved
0.6762	Remote Similarity	NPD5281	Approved
0.6757	Remote Similarity	NPD4754	Approved
0.6757	Remote Similarity	NPD5174	Approved
0.6757	Remote Similarity	NPD5175	Approved
0.6754	Remote Similarity	NPD6014	Approved
0.6754	Remote Similarity	NPD6012	Approved
0.6754	Remote Similarity	NPD6013	Approved
0.6731	Remote Similarity	NPD6904	Approved
0.6731	Remote Similarity	NPD6673	Approved
0.6731	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6080	Approved
0.6729	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6882	Approved
0.6721	Remote Similarity	NPD8328	Phase 3
0.6703	Remote Similarity	NPD7331	Phase 2
0.67	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3573	Approved
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6637	Remote Similarity	NPD4768	Approved
0.6637	Remote Similarity	NPD4767	Approved
0.6634	Remote Similarity	NPD4788	Approved
0.6613	Remote Similarity	NPD6616	Approved
0.6604	Remote Similarity	NPD6050	Approved
0.66	Remote Similarity	NPD5369	Approved
0.6593	Remote Similarity	NPD7341	Phase 2
0.6581	Remote Similarity	NPD6053	Discontinued
0.656	Remote Similarity	NPD7078	Approved
0.656	Remote Similarity	NPD8293	Discontinued
0.6552	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD4730	Approved
0.6522	Remote Similarity	NPD5128	Approved
0.6522	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4729	Approved
0.6518	Remote Similarity	NPD5091	Approved
0.6514	Remote Similarity	NPD7614	Phase 1
0.6509	Remote Similarity	NPD5692	Phase 3
0.6509	Remote Similarity	NPD5785	Approved
0.6509	Remote Similarity	NPD5207	Approved
0.6508	Remote Similarity	NPD6033	Approved
0.6508	Remote Similarity	NPD7736	Approved
0.6505	Remote Similarity	NPD1694	Approved
0.65	Remote Similarity	NPD6009	Approved
0.6484	Remote Similarity	NPD7260	Phase 2
0.6476	Remote Similarity	NPD5208	Approved
0.6471	Remote Similarity	NPD6110	Phase 1
0.6466	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7319	Approved
0.6452	Remote Similarity	NPD7604	Phase 2
0.6449	Remote Similarity	NPD5693	Phase 1
0.6449	Remote Similarity	NPD5694	Approved
0.6446	Remote Similarity	NPD6335	Approved
0.6442	Remote Similarity	NPD5786	Approved
0.6442	Remote Similarity	NPD6098	Approved
0.6429	Remote Similarity	NPD6933	Approved
0.6423	Remote Similarity	NPD5983	Phase 2
0.6417	Remote Similarity	NPD6274	Approved
0.6417	Remote Similarity	NPD6868	Approved
0.641	Remote Similarity	NPD5247	Approved
0.641	Remote Similarity	NPD5135	Approved
0.641	Remote Similarity	NPD5249	Phase 3
0.641	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5248	Approved
0.641	Remote Similarity	NPD5250	Approved
0.641	Remote Similarity	NPD5251	Approved
0.641	Remote Similarity	NPD5169	Approved
0.64	Remote Similarity	NPD4195	Approved
0.6396	Remote Similarity	NPD7638	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6381	Remote Similarity	NPD7524	Approved
0.6379	Remote Similarity	NPD5168	Approved
0.6364	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7732	Phase 3
0.6356	Remote Similarity	NPD5217	Approved
0.6356	Remote Similarity	NPD5127	Approved
0.6356	Remote Similarity	NPD5215	Approved
0.6356	Remote Similarity	NPD5216	Approved
0.6355	Remote Similarity	NPD4096	Approved
0.6349	Remote Similarity	NPD6336	Discontinued
0.6349	Remote Similarity	NPD7507	Approved
0.6346	Remote Similarity	NPD5363	Approved
0.6339	Remote Similarity	NPD7640	Approved
0.6339	Remote Similarity	NPD7639	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