NPASS Compound

Structure

NPC472750 OpenBabel07101719252D 32 34 0 0 1 0 0 0 0 0999 V2000 5.6557 -0.9872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6901 0.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8456 -1.4018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4276 -1.7347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2008 -3.1573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7645 -3.1573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2768 -0.3610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6874 -1.8125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0765 -1.5819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2655 -2.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4188 -0.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9908 -1.1409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2802 -0.6972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7789 -0.5834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8873 -1.2855 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1965 -0.7974 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4991 -0.2620 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8292 -2.1863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1139 -0.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8194 -0.7259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5721 -0.4871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0628 -0.2620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2819 -2.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3831 -0.7259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5637 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0252 0.2241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7220 -0.3836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7030 0.4606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6359 0.9626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3258 -1.2946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6367 -1.6573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 15 3 1 6 0 0 0 15 20 1 0 0 0 0 16 4 1 6 0 0 0 16 21 1 0 0 0 0 17 13 1 1 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 9 1 1 0 0 0 18 23 1 0 0 0 0 18 32 1 0 0 0 0 19 26 2 0 0 0 0 19 30 1 0 0 0 0 20 27 2 0 0 0 0 21 25 1 6 0 0 0 21 30 1 0 0 0 0 22 24 1 1 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 24 7 1 1 0 0 0 24 32 1 0 0 0 0 25 29 1 1 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.26
Volume:	466.272
LogP:	3.688
LogD:	1.234
LogS:	-3.11
# Rotatable Bonds:	3
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	6.773
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.716
MDCK Permeability:	1.0992240277118981e-05
Pgp-inhibitor:	0.584
Pgp-substrate:	0.648
Human Intestinal Absorption (HIA):	0.201
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.49

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.924
Plasma Protein Binding (PPB):	94.28063201904297%
Volume Distribution (VD):	2.314
Pgp-substrate:	4.869637966156006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.529
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.566
CYP3A4-inhibitor:	0.641
CYP3A4-substrate:	0.361

ADMET: Excretion

Clearance (CL):	9.393
Half-life (T1/2):	0.356

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.754
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.711
Maximum Recommended Daily Dose:	0.736
Skin Sensitization:	0.23
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC472750

Natural Product ID:	NPC472750
*Common Name:**	LWBOLXISYJZCPC-BBMYCWDOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LWBOLXISYJZCPC-BBMYCWDOSA-N
Standard InCHI:	InChI=1S/C25H38O7/c1-14(2)12-19(26)30-21-16(4)13-17-20(27)15(3)8-10-23(5,6)18-9-11-24(7,32-18)22(28)25(21,29)31-17/h8,10,12,15-18,21-22,28-29H,9,11,13H2,1-7H3/b10-8+/t15-,16+,17+,18-,21+,22-,24+,25-/m0/s1
SMILES:	CC1CC2C(=O)C(C=CC(C3CCC(O3)(C(C(C1OC(=O)C=C(C)C)(O2)O)O)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581997
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]

☑ 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
EC50	1
Others	5

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[507939]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[507939]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[507939]
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	=	47.0	%	PMID[507939]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	=	20.0	%	PMID[507939]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	222000.0	nM	PMID[507939]

☑ 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 NPC472750 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	1057
0.2-0.3	3956
0.3-0.4	7390
0.4-0.5	13686
0.5-0.6	7679
0.6-0.7	6317
0.7-0.8	2330
0.8-0.85	70
0.85-0.9	14
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472747
0.9896	High Similarity	NPC472748
0.9794	High Similarity	NPC472749
0.9794	High Similarity	NPC472751
0.9381	High Similarity	NPC472753
0.9286	High Similarity	NPC472754
0.9	High Similarity	NPC472755
0.8911	High Similarity	NPC472756
0.8447	Intermediate Similarity	NPC475871
0.8447	Intermediate Similarity	NPC475945
0.8431	Intermediate Similarity	NPC476270
0.8384	Intermediate Similarity	NPC71589
0.8367	Intermediate Similarity	NPC184463
0.8367	Intermediate Similarity	NPC30515
0.835	Intermediate Similarity	NPC474747
0.835	Intermediate Similarity	NPC149371
0.835	Intermediate Similarity	NPC320019
0.835	Intermediate Similarity	NPC324017
0.8318	Intermediate Similarity	NPC5103
0.8304	Intermediate Similarity	NPC107338
0.8304	Intermediate Similarity	NPC109607
0.83	Intermediate Similarity	NPC36954
0.8286	Intermediate Similarity	NPC476740
0.8286	Intermediate Similarity	NPC476738
0.8283	Intermediate Similarity	NPC475912
0.8283	Intermediate Similarity	NPC476300
0.8269	Intermediate Similarity	NPC309398
0.8269	Intermediate Similarity	NPC4620
0.8265	Intermediate Similarity	NPC474761
0.8265	Intermediate Similarity	NPC476004
0.8265	Intermediate Similarity	NPC51004
0.8257	Intermediate Similarity	NPC469463
0.8257	Intermediate Similarity	NPC469454
0.8257	Intermediate Similarity	NPC469496
0.8252	Intermediate Similarity	NPC185141
0.8252	Intermediate Similarity	NPC47880
0.8252	Intermediate Similarity	NPC46998
0.8252	Intermediate Similarity	NPC474742
0.8252	Intermediate Similarity	NPC128733
0.8252	Intermediate Similarity	NPC110443
0.8252	Intermediate Similarity	NPC133907
0.8252	Intermediate Similarity	NPC15993
0.8229	Intermediate Similarity	NPC311163
0.8214	Intermediate Similarity	NPC475775
0.8214	Intermediate Similarity	NPC476529
0.8208	Intermediate Similarity	NPC474421
0.8208	Intermediate Similarity	NPC72813
0.8208	Intermediate Similarity	NPC326994
0.8208	Intermediate Similarity	NPC324327
0.8208	Intermediate Similarity	NPC194620
0.819	Intermediate Similarity	NPC220964
0.819	Intermediate Similarity	NPC203659
0.819	Intermediate Similarity	NPC475676
0.819	Intermediate Similarity	NPC474741
0.8182	Intermediate Similarity	NPC470373
0.8182	Intermediate Similarity	NPC470379
0.8174	Intermediate Similarity	NPC470922
0.8173	Intermediate Similarity	NPC473596
0.8163	Intermediate Similarity	NPC307411
0.8144	Intermediate Similarity	NPC179659
0.8137	Intermediate Similarity	NPC40812
0.8131	Intermediate Similarity	NPC14862
0.8131	Intermediate Similarity	NPC169888
0.8131	Intermediate Similarity	NPC233379
0.8131	Intermediate Similarity	NPC474664
0.8131	Intermediate Similarity	NPC327286
0.8131	Intermediate Similarity	NPC55972
0.8119	Intermediate Similarity	NPC270013
0.8119	Intermediate Similarity	NPC14961
0.8113	Intermediate Similarity	NPC9303
0.8113	Intermediate Similarity	NPC16313
0.8108	Intermediate Similarity	NPC152199
0.8108	Intermediate Similarity	NPC134869
0.8108	Intermediate Similarity	NPC235539
0.81	Intermediate Similarity	NPC162205
0.81	Intermediate Similarity	NPC212486
0.81	Intermediate Similarity	NPC179746
0.81	Intermediate Similarity	NPC81419
0.81	Intermediate Similarity	NPC295204
0.81	Intermediate Similarity	NPC273579
0.81	Intermediate Similarity	NPC288240
0.8095	Intermediate Similarity	NPC474581
0.8095	Intermediate Similarity	NPC475367
0.8095	Intermediate Similarity	NPC473816
0.8095	Intermediate Similarity	NPC110989
0.8081	Intermediate Similarity	NPC473448
0.8077	Intermediate Similarity	NPC164598
0.8077	Intermediate Similarity	NPC201718
0.8077	Intermediate Similarity	NPC474339
0.8073	Intermediate Similarity	NPC304180
0.8073	Intermediate Similarity	NPC179798
0.8061	Intermediate Similarity	NPC202672
0.8058	Intermediate Similarity	NPC187268
0.8058	Intermediate Similarity	NPC83895
0.8058	Intermediate Similarity	NPC187761
0.8058	Intermediate Similarity	NPC471144
0.8056	Intermediate Similarity	NPC15218
0.8056	Intermediate Similarity	NPC38154
0.8056	Intermediate Similarity	NPC313668
0.8056	Intermediate Similarity	NPC315836
0.8039	Intermediate Similarity	NPC476315
0.8037	Intermediate Similarity	NPC477513
0.8036	Intermediate Similarity	NPC23046
0.8021	Intermediate Similarity	NPC9868
0.802	Intermediate Similarity	NPC474035
0.802	Intermediate Similarity	NPC81386
0.802	Intermediate Similarity	NPC121825
0.802	Intermediate Similarity	NPC190294
0.8019	Intermediate Similarity	NPC258532
0.8018	Intermediate Similarity	NPC18547
0.8018	Intermediate Similarity	NPC474906
0.8	Intermediate Similarity	NPC12172
0.8	Intermediate Similarity	NPC225353
0.8	Intermediate Similarity	NPC208886
0.8	Intermediate Similarity	NPC329952
0.7965	Intermediate Similarity	NPC297179
0.7963	Intermediate Similarity	NPC193765
0.7963	Intermediate Similarity	NPC475960
0.7963	Intermediate Similarity	NPC473807
0.7961	Intermediate Similarity	NPC328562
0.7961	Intermediate Similarity	NPC120299
0.7961	Intermediate Similarity	NPC266842
0.7961	Intermediate Similarity	NPC323421
0.7946	Intermediate Similarity	NPC470628
0.7946	Intermediate Similarity	NPC474046
0.7946	Intermediate Similarity	NPC259306
0.7944	Intermediate Similarity	NPC475802
0.7938	Intermediate Similarity	NPC471494
0.7928	Intermediate Similarity	NPC51978
0.7928	Intermediate Similarity	NPC56448
0.7925	Intermediate Similarity	NPC475873
0.7921	Intermediate Similarity	NPC469645
0.7921	Intermediate Similarity	NPC469692
0.7909	Intermediate Similarity	NPC126897
0.7909	Intermediate Similarity	NPC201992
0.7909	Intermediate Similarity	NPC317107
0.7909	Intermediate Similarity	NPC297945
0.7905	Intermediate Similarity	NPC472643
0.79	Intermediate Similarity	NPC473619
0.789	Intermediate Similarity	NPC475922
0.7885	Intermediate Similarity	NPC222303
0.7885	Intermediate Similarity	NPC261377
0.7885	Intermediate Similarity	NPC475653
0.7885	Intermediate Similarity	NPC473326
0.7885	Intermediate Similarity	NPC308567
0.7885	Intermediate Similarity	NPC255592
0.7876	Intermediate Similarity	NPC473590
0.7876	Intermediate Similarity	NPC471146
0.7876	Intermediate Similarity	NPC473968
0.7876	Intermediate Similarity	NPC471145
0.7864	Intermediate Similarity	NPC76862
0.7864	Intermediate Similarity	NPC158416
0.7864	Intermediate Similarity	NPC255410
0.7864	Intermediate Similarity	NPC288350
0.7864	Intermediate Similarity	NPC470883
0.7864	Intermediate Similarity	NPC173329
0.7864	Intermediate Similarity	NPC39859
0.7864	Intermediate Similarity	NPC31645
0.7857	Intermediate Similarity	NPC469877
0.7857	Intermediate Similarity	NPC470919
0.785	Intermediate Similarity	NPC100487
0.7843	Intermediate Similarity	NPC256368
0.7843	Intermediate Similarity	NPC469632
0.7838	Intermediate Similarity	NPC11252
0.7838	Intermediate Similarity	NPC317687
0.7838	Intermediate Similarity	NPC289312
0.7835	Intermediate Similarity	NPC243618
0.7835	Intermediate Similarity	NPC70424
0.7833	Intermediate Similarity	NPC213634
0.783	Intermediate Similarity	NPC471148
0.7826	Intermediate Similarity	NPC48692
0.7822	Intermediate Similarity	NPC219874
0.7822	Intermediate Similarity	NPC473321
0.7818	Intermediate Similarity	NPC115257
0.7818	Intermediate Similarity	NPC83005
0.7818	Intermediate Similarity	NPC41551
0.7818	Intermediate Similarity	NPC161816
0.781	Intermediate Similarity	NPC288876
0.781	Intermediate Similarity	NPC475949
0.781	Intermediate Similarity	NPC475053
0.781	Intermediate Similarity	NPC472644
0.7807	Intermediate Similarity	NPC475401
0.7807	Intermediate Similarity	NPC13710
0.78	Intermediate Similarity	NPC173926
0.78	Intermediate Similarity	NPC133450
0.78	Intermediate Similarity	NPC474951
0.7798	Intermediate Similarity	NPC392
0.7798	Intermediate Similarity	NPC219900
0.7798	Intermediate Similarity	NPC177524
0.7788	Intermediate Similarity	NPC69385
0.7788	Intermediate Similarity	NPC328374
0.7788	Intermediate Similarity	NPC40632
0.7788	Intermediate Similarity	NPC251236
0.7788	Intermediate Similarity	NPC96312
0.7788	Intermediate Similarity	NPC134454
0.7788	Intermediate Similarity	NPC17326
0.7787	Intermediate Similarity	NPC471234
0.7778	Intermediate Similarity	NPC248602
0.7778	Intermediate Similarity	NPC127609
0.7778	Intermediate Similarity	NPC477125

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 NPC472750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1397
0.2-0.3	3571
0.3-0.4	2542
0.4-0.5	902
0.5-0.6	324
0.6-0.7	200
0.7-0.8	56
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
0.8081	Intermediate Similarity	NPD6698	Approved
0.8081	Intermediate Similarity	NPD46	Approved
0.7909	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6686	Approved
0.7596	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5282	Discontinued
0.75	Intermediate Similarity	NPD6371	Approved
0.7476	Intermediate Similarity	NPD7983	Approved
0.7383	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7838	Discovery
0.7273	Intermediate Similarity	NPD7492	Approved
0.7227	Intermediate Similarity	NPD6054	Approved
0.7217	Intermediate Similarity	NPD6882	Approved
0.7217	Intermediate Similarity	NPD8297	Approved
0.7213	Intermediate Similarity	NPD6616	Approved
0.7213	Intermediate Similarity	NPD7507	Approved
0.7196	Intermediate Similarity	NPD7839	Suspended
0.7168	Intermediate Similarity	NPD6899	Approved
0.7168	Intermediate Similarity	NPD6881	Approved
0.7168	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8515	Approved
0.7167	Intermediate Similarity	NPD8517	Approved
0.7167	Intermediate Similarity	NPD8513	Phase 3
0.7167	Intermediate Similarity	NPD8516	Approved
0.7154	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7119	Intermediate Similarity	NPD6009	Approved
0.7107	Intermediate Similarity	NPD6370	Approved
0.7097	Intermediate Similarity	NPD7736	Approved
0.7083	Intermediate Similarity	NPD6319	Approved
0.7083	Intermediate Similarity	NPD6059	Approved
0.708	Intermediate Similarity	NPD6412	Phase 2
0.708	Intermediate Similarity	NPD5697	Approved
0.7075	Intermediate Similarity	NPD5778	Approved
0.7075	Intermediate Similarity	NPD5779	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.7059	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8328	Phase 3
0.7048	Intermediate Similarity	NPD5785	Approved
0.7043	Intermediate Similarity	NPD7290	Approved
0.7043	Intermediate Similarity	NPD7102	Approved
0.7043	Intermediate Similarity	NPD6883	Approved
0.704	Intermediate Similarity	NPD7319	Approved
0.7025	Intermediate Similarity	NPD6016	Approved
0.7025	Intermediate Similarity	NPD6015	Approved
0.7018	Intermediate Similarity	NPD7320	Approved
0.7016	Intermediate Similarity	NPD8293	Discontinued
0.7009	Intermediate Similarity	NPD4632	Approved
0.6983	Remote Similarity	NPD6617	Approved
0.6983	Remote Similarity	NPD6847	Approved
0.6983	Remote Similarity	NPD8130	Phase 1
0.6983	Remote Similarity	NPD6650	Approved
0.6983	Remote Similarity	NPD6869	Approved
0.6983	Remote Similarity	NPD6649	Approved
0.6981	Remote Similarity	NPD6411	Approved
0.6975	Remote Similarity	NPD7115	Discovery
0.6972	Remote Similarity	NPD6084	Phase 2
0.6972	Remote Similarity	NPD6083	Phase 2
0.6967	Remote Similarity	NPD5988	Approved
0.6957	Remote Similarity	NPD6013	Approved
0.6957	Remote Similarity	NPD6012	Approved
0.6957	Remote Similarity	NPD6014	Approved
0.6957	Remote Similarity	NPD6372	Approved
0.6957	Remote Similarity	NPD6373	Approved
0.6937	Remote Similarity	NPD5344	Discontinued
0.6931	Remote Similarity	NPD6435	Approved
0.693	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD6053	Discontinued
0.6911	Remote Similarity	NPD7642	Approved
0.688	Remote Similarity	NPD8074	Phase 3
0.687	Remote Similarity	NPD6011	Approved
0.6863	Remote Similarity	NPD7154	Phase 3
0.6829	Remote Similarity	NPD8080	Discontinued
0.681	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7260	Phase 2
0.6796	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6101	Approved
0.6789	Remote Similarity	NPD5695	Phase 3
0.6777	Remote Similarity	NPD7641	Discontinued
0.6774	Remote Similarity	NPD7830	Approved
0.6774	Remote Similarity	NPD7604	Phase 2
0.6774	Remote Similarity	NPD7829	Approved
0.6757	Remote Similarity	NPD7638	Approved
0.6748	Remote Similarity	NPD5983	Phase 2
0.6748	Remote Similarity	NPD8444	Approved
0.6733	Remote Similarity	NPD5368	Approved
0.6731	Remote Similarity	NPD1694	Approved
0.67	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6110	Phase 1
0.6696	Remote Similarity	NPD7640	Approved
0.6696	Remote Similarity	NPD7639	Approved
0.6695	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD8451	Approved
0.6641	Remote Similarity	NPD8415	Approved
0.6639	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD7328	Approved
0.6614	Remote Similarity	NPD8448	Approved
0.6613	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8033	Approved
0.6613	Remote Similarity	NPD7503	Approved
0.661	Remote Similarity	NPD4634	Approved
0.6607	Remote Similarity	NPD5696	Approved
0.6604	Remote Similarity	NPD4251	Approved
0.6604	Remote Similarity	NPD4250	Approved
0.6602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7100	Approved
0.6585	Remote Similarity	NPD7516	Approved
0.6585	Remote Similarity	NPD7101	Approved
0.6583	Remote Similarity	NPD8133	Approved
0.6579	Remote Similarity	NPD5211	Phase 2
0.6571	Remote Similarity	NPD5363	Approved
0.6569	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4821	Approved
0.6569	Remote Similarity	NPD4822	Approved
0.6569	Remote Similarity	NPD4819	Approved
0.6569	Remote Similarity	NPD4820	Approved
0.6562	Remote Similarity	NPD6033	Approved
0.6549	Remote Similarity	NPD6648	Approved
0.6549	Remote Similarity	NPD4696	Approved
0.6549	Remote Similarity	NPD5285	Approved
0.6549	Remote Similarity	NPD5286	Approved
0.6542	Remote Similarity	NPD5737	Approved
0.6542	Remote Similarity	NPD6672	Approved
0.6538	Remote Similarity	NPD5362	Discontinued
0.6532	Remote Similarity	NPD8294	Approved
0.6532	Remote Similarity	NPD8377	Approved
0.6518	Remote Similarity	NPD4755	Approved
0.6514	Remote Similarity	NPD7637	Suspended
0.6514	Remote Similarity	NPD5693	Phase 1
0.6509	Remote Similarity	NPD4249	Approved
0.6505	Remote Similarity	NPD5369	Approved
0.6504	Remote Similarity	NPD6335	Approved
0.6489	Remote Similarity	NPD6845	Suspended
0.6481	Remote Similarity	NPD1695	Approved
0.648	Remote Similarity	NPD8378	Approved
0.648	Remote Similarity	NPD8335	Approved
0.648	Remote Similarity	NPD8296	Approved
0.648	Remote Similarity	NPD8380	Approved
0.648	Remote Similarity	NPD6921	Approved
0.648	Remote Similarity	NPD8379	Approved
0.6475	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5141	Approved
0.6462	Remote Similarity	NPD8390	Approved
0.6462	Remote Similarity	NPD8392	Approved
0.6462	Remote Similarity	NPD8391	Approved
0.6457	Remote Similarity	NPD8299	Approved
0.6457	Remote Similarity	NPD8341	Approved
0.6457	Remote Similarity	NPD8340	Approved
0.6457	Remote Similarity	NPD8342	Approved
0.6455	Remote Similarity	NPD6399	Phase 3
0.6442	Remote Similarity	NPD4269	Approved
0.6442	Remote Similarity	NPD4270	Approved
0.6435	Remote Similarity	NPD5226	Approved
0.6435	Remote Similarity	NPD5225	Approved
0.6435	Remote Similarity	NPD4633	Approved
0.6435	Remote Similarity	NPD5224	Approved
0.6423	Remote Similarity	NPD6317	Approved
0.641	Remote Similarity	NPD6008	Approved
0.6404	Remote Similarity	NPD4700	Approved
0.64	Remote Similarity	NPD8039	Approved
0.6387	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5175	Approved
0.6379	Remote Similarity	NPD5174	Approved
0.6373	Remote Similarity	NPD4268	Approved
0.6373	Remote Similarity	NPD4271	Approved
0.6371	Remote Similarity	NPD6313	Approved
0.6371	Remote Similarity	NPD6314	Approved
0.6349	Remote Similarity	NPD6909	Approved
0.6349	Remote Similarity	NPD6908	Approved
0.6348	Remote Similarity	NPD5223	Approved
0.6341	Remote Similarity	NPD6868	Approved
0.6336	Remote Similarity	NPD5956	Approved
0.633	Remote Similarity	NPD4753	Phase 2
0.633	Remote Similarity	NPD6904	Approved
0.633	Remote Similarity	NPD6080	Approved
0.633	Remote Similarity	NPD6673	Approved
0.6296	Remote Similarity	NPD7524	Approved
0.629	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5209	Approved
0.6283	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5221	Approved
0.6283	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5222	Approved
0.6281	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8273	Phase 1
0.6275	Remote Similarity	NPD4756	Discovery
0.627	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6082	Clinical (unspecified phase)

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