NPASS Compound

Structure

NPC472728 OpenBabel07101718232D 37 39 0 0 1 0 0 0 0 0999 V2000 -2.5700 -3.2410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1431 -2.9399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1431 -1.2963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1090 1.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 1.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0788 -1.4078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4326 0.6055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6485 0.0710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4765 2.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3473 -1.2963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6534 -2.9954 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 2.7197 -2.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2872 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 -0.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2963 -1.2963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1584 1.5043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6436 0.9489 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 3.2872 0.9489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4078 -2.0788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6436 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4815 1.2270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6314 0.9464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4912 -1.8332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1228 1.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5362 0.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5776 1.0173 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 0.1798 -2.5042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0186 2.5773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6436 1.8979 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9894 1.8722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2468 0.3241 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 30 1 0 0 0 0 26 34 2 0 0 0 0 27 32 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:	6.754
LogD:	5.42
LogS:	-5.166
# 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:	6.037
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:	-4.981
MDCK Permeability:	1.4800150893279351e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.085
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.473
Plasma Protein Binding (PPB):	93.17169952392578%
Volume Distribution (VD):	1.805
Pgp-substrate:	4.435008525848389%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.277
CYP2C9-substrate:	0.208
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	11.114
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.751
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.02
Carcinogencity:	0.72
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.805

Download Data

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

Natural Product: NPC472728

Natural Product ID:	NPC472728
*Common Name:**	IDXNDMRSSYBBIJ-WGCTUJHDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IDXNDMRSSYBBIJ-WGCTUJHDSA-N
Standard InCHI:	InChI=1S/C32H48O5/c1-11-21(6)25(33)32-27-23(17-24(37-27)29(7,8)36)26(34)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:	CCC(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:	CHEMBL3581912
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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	23700.0	nM	PMID[469517]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	15.03	%	PMID[469518]

☑ 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 NPC472728 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	200
0.1-0.2	1265
0.2-0.3	4697
0.3-0.4	9227
0.4-0.5	13703
0.5-0.6	7872
0.6-0.7	5118
0.7-0.8	558
0.8-0.85	14
0.85-0.9	6
0.9-0.95	21
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472727
0.9891	High Similarity	NPC177680
0.9891	High Similarity	NPC153776
0.9891	High Similarity	NPC472729
0.9891	High Similarity	NPC472730
0.9783	High Similarity	NPC472732
0.9783	High Similarity	NPC472731
0.9674	High Similarity	NPC472734
0.9674	High Similarity	NPC472733
0.9263	High Similarity	NPC203388
0.9263	High Similarity	NPC471331
0.9263	High Similarity	NPC472687
0.9263	High Similarity	NPC99657
0.9263	High Similarity	NPC471330
0.9255	High Similarity	NPC21681
0.9255	High Similarity	NPC472675
0.9158	High Similarity	NPC27105
0.89	High Similarity	NPC471332
0.89	High Similarity	NPC471333
0.8842	High Similarity	NPC469819
0.8842	High Similarity	NPC114162
0.8602	High Similarity	NPC38885
0.8571	High Similarity	NPC239895
0.8265	Intermediate Similarity	NPC477241
0.8218	Intermediate Similarity	NPC46761
0.8152	Intermediate Similarity	NPC189237
0.8152	Intermediate Similarity	NPC472684
0.8152	Intermediate Similarity	NPC44963
0.81	Intermediate Similarity	NPC93271
0.81	Intermediate Similarity	NPC135576
0.8077	Intermediate Similarity	NPC13385
0.8058	Intermediate Similarity	NPC163249
0.7963	Intermediate Similarity	NPC324683
0.7961	Intermediate Similarity	NPC477870
0.7961	Intermediate Similarity	NPC476213
0.7961	Intermediate Similarity	NPC476134
0.7961	Intermediate Similarity	NPC477871
0.7961	Intermediate Similarity	NPC476246
0.7961	Intermediate Similarity	NPC101067
0.7921	Intermediate Similarity	NPC473164
0.7909	Intermediate Similarity	NPC247069
0.7885	Intermediate Similarity	NPC476126
0.7885	Intermediate Similarity	NPC473163
0.7885	Intermediate Similarity	NPC476235
0.787	Intermediate Similarity	NPC239097
0.7864	Intermediate Similarity	NPC54705
0.7843	Intermediate Similarity	NPC477267
0.7843	Intermediate Similarity	NPC473161
0.7843	Intermediate Similarity	NPC472690
0.7843	Intermediate Similarity	NPC124246
0.7843	Intermediate Similarity	NPC472689
0.7843	Intermediate Similarity	NPC477268
0.783	Intermediate Similarity	NPC478052
0.783	Intermediate Similarity	NPC32006
0.783	Intermediate Similarity	NPC85529
0.783	Intermediate Similarity	NPC292588
0.7822	Intermediate Similarity	NPC473170
0.781	Intermediate Similarity	NPC474330
0.781	Intermediate Similarity	NPC474207
0.7788	Intermediate Similarity	NPC475867
0.7788	Intermediate Similarity	NPC270155
0.7778	Intermediate Similarity	NPC472325
0.7778	Intermediate Similarity	NPC470257
0.7767	Intermediate Similarity	NPC147954
0.7745	Intermediate Similarity	NPC471775
0.7736	Intermediate Similarity	NPC40170
0.7723	Intermediate Similarity	NPC473172
0.7723	Intermediate Similarity	NPC318332
0.7706	Intermediate Similarity	NPC473627
0.7692	Intermediate Similarity	NPC110149
0.7684	Intermediate Similarity	NPC212083
0.767	Intermediate Similarity	NPC273269
0.7667	Intermediate Similarity	NPC316553
0.7658	Intermediate Similarity	NPC326264
0.7653	Intermediate Similarity	NPC99909
0.7642	Intermediate Similarity	NPC320294
0.7642	Intermediate Similarity	NPC264048
0.7642	Intermediate Similarity	NPC239716
0.7642	Intermediate Similarity	NPC475321
0.7636	Intermediate Similarity	NPC474229
0.7636	Intermediate Similarity	NPC43775
0.7634	Intermediate Similarity	NPC478246
0.7634	Intermediate Similarity	NPC478247
0.7629	Intermediate Similarity	NPC79573
0.7624	Intermediate Similarity	NPC61275
0.7624	Intermediate Similarity	NPC474807
0.76	Intermediate Similarity	NPC469464
0.7593	Intermediate Similarity	NPC43285
0.7593	Intermediate Similarity	NPC58370
0.7579	Intermediate Similarity	NPC327002
0.7576	Intermediate Similarity	NPC143025
0.7576	Intermediate Similarity	NPC474854
0.7573	Intermediate Similarity	NPC8803
0.7573	Intermediate Similarity	NPC269492
0.757	Intermediate Similarity	NPC255309
0.757	Intermediate Similarity	NPC470104
0.7568	Intermediate Similarity	NPC205534
0.7568	Intermediate Similarity	NPC193948
0.7551	Intermediate Similarity	NPC477479
0.7551	Intermediate Similarity	NPC477478
0.7551	Intermediate Similarity	NPC203795
0.7551	Intermediate Similarity	NPC470345
0.7551	Intermediate Similarity	NPC229717
0.7549	Intermediate Similarity	NPC196227
0.7549	Intermediate Similarity	NPC472977
0.7549	Intermediate Similarity	NPC67831
0.7549	Intermediate Similarity	NPC472976
0.7549	Intermediate Similarity	NPC174051
0.7549	Intermediate Similarity	NPC473162
0.7547	Intermediate Similarity	NPC473928
0.7547	Intermediate Similarity	NPC80781
0.7545	Intermediate Similarity	NPC37116
0.7527	Intermediate Similarity	NPC325946
0.7525	Intermediate Similarity	NPC471329
0.7525	Intermediate Similarity	NPC262870
0.7525	Intermediate Similarity	NPC146852
0.7525	Intermediate Similarity	NPC116726
0.7525	Intermediate Similarity	NPC475441
0.7525	Intermediate Similarity	NPC296114
0.7525	Intermediate Similarity	NPC19114
0.7524	Intermediate Similarity	NPC316964
0.7524	Intermediate Similarity	NPC198880
0.7524	Intermediate Similarity	NPC112167
0.7523	Intermediate Similarity	NPC318363
0.7523	Intermediate Similarity	NPC473482
0.7523	Intermediate Similarity	NPC475418
0.75	Intermediate Similarity	NPC471999
0.75	Intermediate Similarity	NPC472929
0.75	Intermediate Similarity	NPC474570
0.75	Intermediate Similarity	NPC96377
0.75	Intermediate Similarity	NPC472074
0.75	Intermediate Similarity	NPC472688
0.75	Intermediate Similarity	NPC102352
0.75	Intermediate Similarity	NPC477943
0.75	Intermediate Similarity	NPC53844
0.75	Intermediate Similarity	NPC294050
0.75	Intermediate Similarity	NPC472676
0.75	Intermediate Similarity	NPC32830
0.75	Intermediate Similarity	NPC472073
0.75	Intermediate Similarity	NPC472000
0.75	Intermediate Similarity	NPC328997
0.7477	Intermediate Similarity	NPC34315
0.7476	Intermediate Similarity	NPC31021
0.7475	Intermediate Similarity	NPC472324
0.7475	Intermediate Similarity	NPC90652
0.7474	Intermediate Similarity	NPC2482
0.7456	Intermediate Similarity	NPC472934
0.7455	Intermediate Similarity	NPC250018
0.7455	Intermediate Similarity	NPC153239
0.7455	Intermediate Similarity	NPC87335
0.7455	Intermediate Similarity	NPC475065
0.7455	Intermediate Similarity	NPC41405
0.7453	Intermediate Similarity	NPC9878
0.7453	Intermediate Similarity	NPC472702
0.7453	Intermediate Similarity	NPC472685
0.7453	Intermediate Similarity	NPC181645
0.7453	Intermediate Similarity	NPC115862
0.7453	Intermediate Similarity	NPC473514
0.7449	Intermediate Similarity	NPC6185
0.7449	Intermediate Similarity	NPC132228
0.7449	Intermediate Similarity	NPC263997
0.7449	Intermediate Similarity	NPC469948
0.7449	Intermediate Similarity	NPC8518
0.7449	Intermediate Similarity	NPC241512
0.7434	Intermediate Similarity	NPC473898
0.7431	Intermediate Similarity	NPC144854
0.7431	Intermediate Similarity	NPC473169
0.7431	Intermediate Similarity	NPC220974
0.7431	Intermediate Similarity	NPC473284
0.7431	Intermediate Similarity	NPC3316
0.7429	Intermediate Similarity	NPC471582
0.7426	Intermediate Similarity	NPC280592
0.7426	Intermediate Similarity	NPC113393
0.7426	Intermediate Similarity	NPC166554
0.7426	Intermediate Similarity	NPC253177
0.7426	Intermediate Similarity	NPC15059
0.7426	Intermediate Similarity	NPC213636
0.7423	Intermediate Similarity	NPC278648
0.7423	Intermediate Similarity	NPC476082
0.7423	Intermediate Similarity	NPC64600
0.7414	Intermediate Similarity	NPC478051
0.7411	Intermediate Similarity	NPC269530
0.7407	Intermediate Similarity	NPC146731
0.7407	Intermediate Similarity	NPC75531
0.7407	Intermediate Similarity	NPC149124
0.7404	Intermediate Similarity	NPC125622
0.7404	Intermediate Similarity	NPC471463
0.74	Intermediate Similarity	NPC470417
0.74	Intermediate Similarity	NPC476708
0.74	Intermediate Similarity	NPC53911
0.7396	Intermediate Similarity	NPC116797
0.7391	Intermediate Similarity	NPC106644
0.7391	Intermediate Similarity	NPC17772
0.7387	Intermediate Similarity	NPC5284
0.7387	Intermediate Similarity	NPC286880
0.7387	Intermediate Similarity	NPC29133
0.7383	Intermediate Similarity	NPC283567
0.7383	Intermediate Similarity	NPC70369
0.7383	Intermediate Similarity	NPC53222
0.7383	Intermediate Similarity	NPC473424

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 NPC472728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1654
0.2-0.3	3889
0.3-0.4	2285
0.4-0.5	728
0.5-0.6	210
0.6-0.7	203
0.7-0.8	4
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
0.7327	Intermediate Similarity	NPD5328	Approved
0.7282	Intermediate Similarity	NPD6399	Phase 3
0.7264	Intermediate Similarity	NPD5696	Approved
0.7212	Intermediate Similarity	NPD5282	Discontinued
0.7212	Intermediate Similarity	NPD7748	Approved
0.72	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3618	Phase 1
0.7184	Intermediate Similarity	NPD6079	Approved
0.7172	Intermediate Similarity	NPD4786	Approved
0.7172	Intermediate Similarity	NPD3665	Phase 1
0.7172	Intermediate Similarity	NPD3666	Approved
0.7172	Intermediate Similarity	NPD3133	Approved
0.717	Intermediate Similarity	NPD7902	Approved
0.7155	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7113	Intermediate Similarity	NPD4695	Discontinued
0.7105	Intermediate Similarity	NPD8297	Approved
0.7075	Intermediate Similarity	NPD4697	Phase 3
0.703	Intermediate Similarity	NPD7146	Approved
0.703	Intermediate Similarity	NPD7521	Approved
0.703	Intermediate Similarity	NPD7334	Approved
0.703	Intermediate Similarity	NPD5330	Approved
0.703	Intermediate Similarity	NPD6684	Approved
0.703	Intermediate Similarity	NPD6409	Approved
0.7027	Intermediate Similarity	NPD7128	Approved
0.7027	Intermediate Similarity	NPD5739	Approved
0.7027	Intermediate Similarity	NPD6675	Approved
0.7027	Intermediate Similarity	NPD6402	Approved
0.7019	Intermediate Similarity	NPD6411	Approved
0.7009	Intermediate Similarity	NPD4755	Approved
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.6991	Remote Similarity	NPD6372	Approved
0.6991	Remote Similarity	NPD6373	Approved
0.699	Remote Similarity	NPD4753	Phase 2
0.6981	Remote Similarity	NPD5695	Phase 3
0.697	Remote Similarity	NPD4221	Approved
0.697	Remote Similarity	NPD4223	Phase 3
0.6964	Remote Similarity	NPD6412	Phase 2
0.6944	Remote Similarity	NPD4225	Approved
0.6931	Remote Similarity	NPD5329	Approved
0.693	Remote Similarity	NPD4634	Approved
0.6916	Remote Similarity	NPD5221	Approved
0.6916	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5222	Approved
0.6903	Remote Similarity	NPD6881	Approved
0.6903	Remote Similarity	NPD6899	Approved
0.6903	Remote Similarity	NPD7320	Approved
0.6893	Remote Similarity	NPD6903	Approved
0.6893	Remote Similarity	NPD6672	Approved
0.6893	Remote Similarity	NPD5737	Approved
0.6893	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7900	Approved
0.6887	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4700	Approved
0.6881	Remote Similarity	NPD4696	Approved
0.6881	Remote Similarity	NPD5286	Approved
0.6881	Remote Similarity	NPD5285	Approved
0.687	Remote Similarity	NPD6650	Approved
0.687	Remote Similarity	NPD8130	Phase 1
0.687	Remote Similarity	NPD6649	Approved
0.6863	Remote Similarity	NPD5279	Phase 3
0.6857	Remote Similarity	NPD7515	Phase 2
0.6852	Remote Similarity	NPD5173	Approved
0.6833	Remote Similarity	NPD6319	Approved
0.6833	Remote Similarity	NPD6059	Approved
0.6833	Remote Similarity	NPD6054	Approved
0.6832	Remote Similarity	NPD3668	Phase 3
0.6832	Remote Similarity	NPD4197	Approved
0.6827	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5223	Approved
0.6814	Remote Similarity	NPD5701	Approved
0.6814	Remote Similarity	NPD5697	Approved
0.6803	Remote Similarity	NPD8328	Phase 3
0.68	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4202	Approved
0.6783	Remote Similarity	NPD7102	Approved
0.6783	Remote Similarity	NPD7290	Approved
0.6783	Remote Similarity	NPD6883	Approved
0.6757	Remote Similarity	NPD5224	Approved
0.6757	Remote Similarity	NPD5211	Phase 2
0.6757	Remote Similarity	NPD5226	Approved
0.6757	Remote Similarity	NPD5225	Approved
0.6757	Remote Similarity	NPD4633	Approved
0.6754	Remote Similarity	NPD6011	Approved
0.6752	Remote Similarity	NPD4632	Approved
0.6735	Remote Similarity	NPD3617	Approved
0.6726	Remote Similarity	NPD6008	Approved
0.6724	Remote Similarity	NPD6869	Approved
0.6724	Remote Similarity	NPD6847	Approved
0.6724	Remote Similarity	NPD6617	Approved
0.6724	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6370	Approved
0.6699	Remote Similarity	NPD4519	Discontinued
0.6699	Remote Similarity	NPD4689	Approved
0.6699	Remote Similarity	NPD4690	Approved
0.6699	Remote Similarity	NPD5280	Approved
0.6699	Remote Similarity	NPD4693	Phase 3
0.6699	Remote Similarity	NPD5205	Approved
0.6699	Remote Similarity	NPD4688	Approved
0.6699	Remote Similarity	NPD4694	Approved
0.6699	Remote Similarity	NPD5690	Phase 2
0.6699	Remote Similarity	NPD4623	Approved
0.6699	Remote Similarity	NPD4138	Approved
0.6698	Remote Similarity	NPD5281	Approved
0.6698	Remote Similarity	NPD5284	Approved
0.6696	Remote Similarity	NPD5174	Approved
0.6696	Remote Similarity	NPD4754	Approved
0.6696	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD6013	Approved
0.6696	Remote Similarity	NPD6014	Approved
0.6696	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6673	Approved
0.664	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6637	Remote Similarity	NPD5141	Approved
0.6636	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD5778	Approved
0.6635	Remote Similarity	NPD3573	Approved
0.6634	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7331	Phase 2
0.6613	Remote Similarity	NPD7492	Approved
0.6609	Remote Similarity	NPD6686	Approved
0.6587	Remote Similarity	NPD7736	Approved
0.6585	Remote Similarity	NPD5988	Approved
0.6579	Remote Similarity	NPD4767	Approved
0.6579	Remote Similarity	NPD4768	Approved
0.6569	Remote Similarity	NPD4788	Approved
0.656	Remote Similarity	NPD6616	Approved
0.6542	Remote Similarity	NPD6050	Approved
0.6535	Remote Similarity	NPD5369	Approved
0.6525	Remote Similarity	NPD6053	Discontinued
0.6522	Remote Similarity	NPD7341	Phase 2
0.6508	Remote Similarity	NPD7078	Approved
0.6496	Remote Similarity	NPD6371	Approved
0.6466	Remote Similarity	NPD5128	Approved
0.6466	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4729	Approved
0.6466	Remote Similarity	NPD4730	Approved
0.646	Remote Similarity	NPD5091	Approved
0.6457	Remote Similarity	NPD6033	Approved
0.6455	Remote Similarity	NPD7732	Phase 3
0.6455	Remote Similarity	NPD7614	Phase 1
0.6449	Remote Similarity	NPD5785	Approved
0.6449	Remote Similarity	NPD5207	Approved
0.6449	Remote Similarity	NPD5692	Phase 3
0.6446	Remote Similarity	NPD6009	Approved
0.6446	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD1694	Approved
0.6436	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7260	Phase 2
0.6415	Remote Similarity	NPD5208	Approved
0.641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6110	Phase 1
0.6406	Remote Similarity	NPD7319	Approved
0.64	Remote Similarity	NPD7604	Phase 2
0.6393	Remote Similarity	NPD6335	Approved
0.6389	Remote Similarity	NPD5693	Phase 1
0.6389	Remote Similarity	NPD8035	Phase 2
0.6389	Remote Similarity	NPD7983	Approved
0.6389	Remote Similarity	NPD5694	Approved
0.6389	Remote Similarity	NPD8034	Phase 2
0.6381	Remote Similarity	NPD6098	Approved
0.6381	Remote Similarity	NPD5786	Approved
0.6379	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5983	Phase 2
0.6364	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD6274	Approved
0.6356	Remote Similarity	NPD5247	Approved
0.6356	Remote Similarity	NPD5251	Approved
0.6356	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5169	Approved
0.6356	Remote Similarity	NPD5135	Approved
0.6356	Remote Similarity	NPD5248	Approved
0.6356	Remote Similarity	NPD5249	Phase 3
0.6356	Remote Similarity	NPD5250	Approved
0.6356	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7100	Approved
0.6341	Remote Similarity	NPD7101	Approved
0.6339	Remote Similarity	NPD7638	Approved
0.6337	Remote Similarity	NPD4195	Approved
0.6325	Remote Similarity	NPD5168	Approved
0.6321	Remote Similarity	NPD7524	Approved
0.6311	Remote Similarity	NPD6317	Approved
0.6303	Remote Similarity	NPD5215	Approved
0.6303	Remote Similarity	NPD5216	Approved
0.6303	Remote Similarity	NPD5127	Approved
0.6303	Remote Similarity	NPD5217	Approved
0.6299	Remote Similarity	NPD7507	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