NPASS Compound

Structure

NPC472232 OpenBabel07101719512D 34 40 0 0 1 0 0 0 0 0999 V2000 -2.4769 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4525 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7475 -4.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7231 -4.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2525 -2.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2525 0.2883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5455 -3.5298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7006 -3.0420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0802 -2.0664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2353 -1.5786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9279 -1.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7006 -0.1152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5455 -0.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3544 -1.0908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9279 0.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9279 1.2771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3904 -1.0908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5013 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5013 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3904 -3.0420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7006 -2.0664 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0802 -3.0420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9279 2.2527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2353 -3.5298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8557 -1.5786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8557 -0.6030 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3904 -2.0664 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5455 -1.5786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9279 -0.3015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9251 -3.5298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2293 3.1806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9512 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 2 19 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 27 1 0 0 0 0 11 14 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 29 1 0 0 0 0 17 27 1 0 0 0 0 17 28 1 0 0 0 0 18 1 1 1 0 0 0 18 23 1 0 0 0 0 19 30 1 1 0 0 0 20 24 1 0 0 0 0 20 27 1 6 0 0 0 21 25 1 6 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 1 0 0 0 23 32 2 0 0 0 0 23 33 1 0 0 0 0 25 26 1 1 0 0 0 26 30 1 1 0 0 0 27 28 1 1 0 0 0 28 13 1 6 0 0 0 29 15 1 1 0 0 0 29 33 1 0 0 0 0 29 34 1 0 0 0 0 30 14 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.35
Volume:	540.811
LogP:	4.853
LogD:	4.275
LogS:	-5.285
# Rotatable Bonds:	2
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	6.371
Fsp3:	0.938
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.268
MDCK Permeability:	2.1911928342888132e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.118

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	94.22942352294922%
Volume Distribution (VD):	1.334
Pgp-substrate:	2.681208848953247%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.718
CYP2C19-inhibitor:	0.16
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.36
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.875

ADMET: Excretion

Clearance (CL):	8.064
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.52
Human Hepatotoxicity (H-HT):	0.505
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.963
Carcinogencity:	0.048
Eye Corrosion:	0.008
Eye Irritation:	0.135
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: NPC472232

Natural Product ID:	NPC472232
*Common Name:**	CXYRTWBYTTYNDF-RLQWGGBLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CXYRTWBYTTYNDF-RLQWGGBLSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18-15-29(33-23(18)32)16-19(2)30(34-29)14-11-25(5)21-8-7-20-24(3,4)22(31)9-10-27(20)17-28(21,27)13-12-26(25,30)6/h18-22,31H,7-17H2,1-6H3/t18-,19-,20+,21-,22-,25+,26+,27-,28-,29+,30-/m1/s1
SMILES:	CC1CC2(CC(C3(O2)CCC4(C3(CCC56C4CCC7C5(C6)CCC(C7(C)C)O)C)C)C)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353849
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO33399	abies faxoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25554367]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	21100.0	nM	PMID[493880]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	25200.0	nM	PMID[493880]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16000.0	nM	PMID[493880]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[493880]

☑ 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 NPC472232 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	432
0.1-0.2	3815
0.2-0.3	13493
0.3-0.4	10349
0.4-0.5	5633
0.5-0.6	5800
0.6-0.7	2652
0.7-0.8	488
0.8-0.85	27
0.85-0.9	3
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472231
0.9425	High Similarity	NPC472234
0.9425	High Similarity	NPC472233
0.875	High Similarity	NPC244969
0.875	High Similarity	NPC213528
0.8721	High Similarity	NPC58631
0.8571	High Similarity	NPC100078
0.8506	High Similarity	NPC472229
0.8506	High Similarity	NPC472230
0.8495	Intermediate Similarity	NPC472238
0.8495	Intermediate Similarity	NPC472237
0.8485	Intermediate Similarity	NPC166079
0.8485	Intermediate Similarity	NPC306776
0.8462	Intermediate Similarity	NPC33398
0.8384	Intermediate Similarity	NPC472227
0.8384	Intermediate Similarity	NPC472228
0.8298	Intermediate Similarity	NPC161035
0.8298	Intermediate Similarity	NPC211845
0.8298	Intermediate Similarity	NPC256104
0.8298	Intermediate Similarity	NPC182740
0.8298	Intermediate Similarity	NPC122083
0.8295	Intermediate Similarity	NPC12933
0.828	Intermediate Similarity	NPC77756
0.8256	Intermediate Similarity	NPC207010
0.8256	Intermediate Similarity	NPC317913
0.8229	Intermediate Similarity	NPC476728
0.8229	Intermediate Similarity	NPC116683
0.8191	Intermediate Similarity	NPC474065
0.8191	Intermediate Similarity	NPC52756
0.8191	Intermediate Similarity	NPC475878
0.814	Intermediate Similarity	NPC4209
0.8125	Intermediate Similarity	NPC21897
0.8125	Intermediate Similarity	NPC305808
0.809	Intermediate Similarity	NPC469745
0.8068	Intermediate Similarity	NPC201276
0.8068	Intermediate Similarity	NPC80891
0.8046	Intermediate Similarity	NPC474404
0.8046	Intermediate Similarity	NPC475031
0.8043	Intermediate Similarity	NPC472272
0.8041	Intermediate Similarity	NPC156377
0.8023	Intermediate Similarity	NPC212733
0.8022	Intermediate Similarity	NPC474996
0.8022	Intermediate Similarity	NPC319909
0.8021	Intermediate Similarity	NPC470424
0.8	Intermediate Similarity	NPC289486
0.8	Intermediate Similarity	NPC61107
0.8	Intermediate Similarity	NPC13494
0.7978	Intermediate Similarity	NPC261616
0.7957	Intermediate Similarity	NPC210658
0.7957	Intermediate Similarity	NPC161928
0.7955	Intermediate Similarity	NPC471045
0.7955	Intermediate Similarity	NPC476732
0.7955	Intermediate Similarity	NPC171426
0.7955	Intermediate Similarity	NPC34046
0.7955	Intermediate Similarity	NPC224802
0.7955	Intermediate Similarity	NPC199965
0.7955	Intermediate Similarity	NPC80089
0.7955	Intermediate Similarity	NPC324700
0.7938	Intermediate Similarity	NPC470031
0.7917	Intermediate Similarity	NPC476189
0.7912	Intermediate Similarity	NPC259173
0.7907	Intermediate Similarity	NPC280026
0.7907	Intermediate Similarity	NPC167702
0.7889	Intermediate Similarity	NPC280781
0.7889	Intermediate Similarity	NPC48756
0.7889	Intermediate Similarity	NPC474870
0.7889	Intermediate Similarity	NPC271572
0.7879	Intermediate Similarity	NPC292775
0.7872	Intermediate Similarity	NPC128475
0.7865	Intermediate Similarity	NPC320144
0.7865	Intermediate Similarity	NPC476176
0.7857	Intermediate Similarity	NPC475765
0.7857	Intermediate Similarity	NPC475785
0.785	Intermediate Similarity	NPC79193
0.7849	Intermediate Similarity	NPC474448
0.7849	Intermediate Similarity	NPC92139
0.7841	Intermediate Similarity	NPC477919
0.7841	Intermediate Similarity	NPC307865
0.7841	Intermediate Similarity	NPC143133
0.7841	Intermediate Similarity	NPC180199
0.7841	Intermediate Similarity	NPC298168
0.7835	Intermediate Similarity	NPC470423
0.7835	Intermediate Similarity	NPC206878
0.7826	Intermediate Similarity	NPC471044
0.7826	Intermediate Similarity	NPC473299
0.7826	Intermediate Similarity	NPC473336
0.7816	Intermediate Similarity	NPC273366
0.7812	Intermediate Similarity	NPC473066
0.7802	Intermediate Similarity	NPC296734
0.7802	Intermediate Similarity	NPC121121
0.7802	Intermediate Similarity	NPC470611
0.7802	Intermediate Similarity	NPC477935
0.78	Intermediate Similarity	NPC108371
0.78	Intermediate Similarity	NPC41843
0.78	Intermediate Similarity	NPC470030
0.7778	Intermediate Similarity	NPC471241
0.7778	Intermediate Similarity	NPC477851
0.7778	Intermediate Similarity	NPC472853
0.7766	Intermediate Similarity	NPC252714
0.7757	Intermediate Similarity	NPC97002
0.7755	Intermediate Similarity	NPC215570
0.7753	Intermediate Similarity	NPC185465
0.7736	Intermediate Similarity	NPC473062
0.7736	Intermediate Similarity	NPC470311
0.7723	Intermediate Similarity	NPC108227
0.7723	Intermediate Similarity	NPC472081
0.7723	Intermediate Similarity	NPC178853
0.7723	Intermediate Similarity	NPC476512
0.7717	Intermediate Similarity	NPC477285
0.7717	Intermediate Similarity	NPC327451
0.7717	Intermediate Similarity	NPC111582
0.7714	Intermediate Similarity	NPC227879
0.7714	Intermediate Similarity	NPC208333
0.7708	Intermediate Similarity	NPC470114
0.77	Intermediate Similarity	NPC473155
0.77	Intermediate Similarity	NPC472144
0.7684	Intermediate Similarity	NPC471221
0.7677	Intermediate Similarity	NPC193785
0.7674	Intermediate Similarity	NPC469940
0.767	Intermediate Similarity	NPC88469
0.766	Intermediate Similarity	NPC80700
0.766	Intermediate Similarity	NPC302111
0.7647	Intermediate Similarity	NPC310138
0.7647	Intermediate Similarity	NPC114700
0.7647	Intermediate Similarity	NPC470029
0.7647	Intermediate Similarity	NPC134967
0.764	Intermediate Similarity	NPC171658
0.764	Intermediate Similarity	NPC23884
0.7619	Intermediate Similarity	NPC472079
0.7615	Intermediate Similarity	NPC475490
0.7614	Intermediate Similarity	NPC179858
0.7609	Intermediate Similarity	NPC317066
0.7609	Intermediate Similarity	NPC242771
0.7609	Intermediate Similarity	NPC477286
0.7609	Intermediate Similarity	NPC164289
0.7609	Intermediate Similarity	NPC328007
0.7609	Intermediate Similarity	NPC475388
0.7609	Intermediate Similarity	NPC311642
0.7609	Intermediate Similarity	NPC286719
0.7609	Intermediate Similarity	NPC30583
0.7609	Intermediate Similarity	NPC100366
0.7609	Intermediate Similarity	NPC477936
0.7609	Intermediate Similarity	NPC24556
0.7604	Intermediate Similarity	NPC56962
0.7604	Intermediate Similarity	NPC24705
0.7604	Intermediate Similarity	NPC61688
0.7604	Intermediate Similarity	NPC228059
0.7604	Intermediate Similarity	NPC200580
0.76	Intermediate Similarity	NPC472273
0.76	Intermediate Similarity	NPC472145
0.76	Intermediate Similarity	NPC253586
0.7586	Intermediate Similarity	NPC232112
0.7586	Intermediate Similarity	NPC109510
0.7582	Intermediate Similarity	NPC470609
0.7582	Intermediate Similarity	NPC248944
0.7582	Intermediate Similarity	NPC7479
0.7582	Intermediate Similarity	NPC257296
0.7579	Intermediate Similarity	NPC5943
0.7579	Intermediate Similarity	NPC202937
0.7576	Intermediate Similarity	NPC205173
0.7573	Intermediate Similarity	NPC97260
0.7573	Intermediate Similarity	NPC476837
0.7573	Intermediate Similarity	NPC139181
0.7558	Intermediate Similarity	NPC477850
0.7558	Intermediate Similarity	NPC477929
0.7556	Intermediate Similarity	NPC472608
0.7556	Intermediate Similarity	NPC329117
0.7553	Intermediate Similarity	NPC62572
0.7553	Intermediate Similarity	NPC232044
0.7553	Intermediate Similarity	NPC266651
0.7553	Intermediate Similarity	NPC273290
0.7553	Intermediate Similarity	NPC235402
0.7551	Intermediate Similarity	NPC35164
0.7549	Intermediate Similarity	NPC477172
0.7528	Intermediate Similarity	NPC472486
0.7528	Intermediate Similarity	NPC477932
0.7528	Intermediate Similarity	NPC477933
0.7528	Intermediate Similarity	NPC471046
0.7528	Intermediate Similarity	NPC472487
0.7527	Intermediate Similarity	NPC470070
0.7527	Intermediate Similarity	NPC472744
0.7526	Intermediate Similarity	NPC18536
0.7526	Intermediate Similarity	NPC50443
0.75	Intermediate Similarity	NPC190940
0.75	Intermediate Similarity	NPC327093
0.75	Intermediate Similarity	NPC77311
0.75	Intermediate Similarity	NPC221993
0.75	Intermediate Similarity	NPC477489
0.75	Intermediate Similarity	NPC73515
0.7477	Intermediate Similarity	NPC98633
0.7476	Intermediate Similarity	NPC470172
0.7475	Intermediate Similarity	NPC151214
0.7475	Intermediate Similarity	NPC477495
0.7475	Intermediate Similarity	NPC175
0.7475	Intermediate Similarity	NPC30687
0.7475	Intermediate Similarity	NPC191915
0.7474	Intermediate Similarity	NPC476727
0.7474	Intermediate Similarity	NPC476726
0.7474	Intermediate Similarity	NPC131365
0.7474	Intermediate Similarity	NPC215968

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 NPC472232 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	463
0.1-0.2	3752
0.2-0.3	3490
0.3-0.4	853
0.4-0.5	269
0.5-0.6	209
0.6-0.7	94
0.7-0.8	20
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
0.8256	Intermediate Similarity	NPD6116	Phase 1
0.814	Intermediate Similarity	NPD6117	Approved
0.7955	Intermediate Similarity	NPD6118	Approved
0.7955	Intermediate Similarity	NPD6115	Approved
0.7955	Intermediate Similarity	NPD6114	Approved
0.7955	Intermediate Similarity	NPD6697	Approved
0.7907	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3702	Approved
0.7582	Intermediate Similarity	NPD6928	Phase 2
0.7471	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5777	Approved
0.7471	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD8034	Phase 2
0.7449	Intermediate Similarity	NPD8035	Phase 2
0.7356	Intermediate Similarity	NPD4245	Approved
0.7356	Intermediate Similarity	NPD4244	Approved
0.7333	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3698	Phase 2
0.7241	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1700	Approved
0.7188	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5360	Phase 3
0.7079	Intermediate Similarity	NPD6081	Approved
0.7059	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3703	Phase 2
0.7027	Intermediate Similarity	NPD6882	Approved
0.6972	Remote Similarity	NPD7320	Approved
0.6966	Remote Similarity	NPD4789	Approved
0.6944	Remote Similarity	NPD7128	Approved
0.6944	Remote Similarity	NPD6402	Approved
0.6944	Remote Similarity	NPD5739	Approved
0.6944	Remote Similarity	NPD6675	Approved
0.6909	Remote Similarity	NPD6372	Approved
0.6909	Remote Similarity	NPD6373	Approved
0.6897	Remote Similarity	NPD4224	Phase 2
0.6863	Remote Similarity	NPD6399	Phase 3
0.6863	Remote Similarity	NPD8171	Discontinued
0.6854	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6881	Approved
0.6818	Remote Similarity	NPD6899	Approved
0.6789	Remote Similarity	NPD6008	Approved
0.6786	Remote Similarity	NPD6650	Approved
0.6786	Remote Similarity	NPD6649	Approved
0.6782	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4787	Phase 1
0.6727	Remote Similarity	NPD5697	Approved
0.6727	Remote Similarity	NPD5701	Approved
0.6703	Remote Similarity	NPD4758	Discontinued
0.6696	Remote Similarity	NPD6883	Approved
0.6696	Remote Similarity	NPD7290	Approved
0.6696	Remote Similarity	NPD7102	Approved
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6637	Remote Similarity	NPD6617	Approved
0.6637	Remote Similarity	NPD8130	Phase 1
0.6637	Remote Similarity	NPD6869	Approved
0.6637	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6847	Approved
0.6635	Remote Similarity	NPD6001	Approved
0.6633	Remote Similarity	NPD4788	Approved
0.6632	Remote Similarity	NPD3671	Phase 1
0.6632	Remote Similarity	NPD5364	Discontinued
0.6612	Remote Similarity	NPD6616	Approved
0.6612	Remote Similarity	NPD7507	Approved
0.661	Remote Similarity	NPD6059	Approved
0.661	Remote Similarity	NPD6054	Approved
0.6607	Remote Similarity	NPD6014	Approved
0.6607	Remote Similarity	NPD6013	Approved
0.6607	Remote Similarity	NPD6012	Approved
0.6604	Remote Similarity	NPD6084	Phase 2
0.6604	Remote Similarity	NPD6083	Phase 2
0.6579	Remote Similarity	NPD8297	Approved
0.6571	Remote Similarity	NPD7991	Discontinued
0.6557	Remote Similarity	NPD8293	Discontinued
0.6542	Remote Similarity	NPD7638	Approved
0.6538	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD6370	Approved
0.6496	Remote Similarity	NPD6009	Approved
0.6481	Remote Similarity	NPD8418	Phase 2
0.6481	Remote Similarity	NPD7640	Approved
0.6481	Remote Similarity	NPD7639	Approved
0.6458	Remote Similarity	NPD4802	Phase 2
0.6458	Remote Similarity	NPD4238	Approved
0.6452	Remote Similarity	NPD7319	Approved
0.6449	Remote Similarity	NPD7902	Approved
0.6449	Remote Similarity	NPD4755	Approved
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6015	Approved
0.641	Remote Similarity	NPD6940	Discontinued
0.6396	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3198	Approved
0.6389	Remote Similarity	NPD5696	Approved
0.6374	Remote Similarity	NPD229	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD7632	Discontinued
0.633	Remote Similarity	NPD5286	Approved
0.633	Remote Similarity	NPD5285	Approved
0.633	Remote Similarity	NPD4696	Approved
0.633	Remote Similarity	NPD4700	Approved
0.6327	Remote Similarity	NPD7525	Registered
0.6321	Remote Similarity	NPD7748	Approved
0.6316	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6903	Approved
0.6311	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7604	Phase 2
0.6303	Remote Similarity	NPD7328	Approved
0.6303	Remote Similarity	NPD6335	Approved
0.6303	Remote Similarity	NPD7327	Approved
0.63	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3669	Approved
0.6286	Remote Similarity	NPD7515	Phase 2
0.6283	Remote Similarity	NPD6412	Phase 2
0.6275	Remote Similarity	NPD6409	Approved
0.6275	Remote Similarity	NPD6684	Approved
0.6275	Remote Similarity	NPD5330	Approved
0.6275	Remote Similarity	NPD3618	Phase 1
0.6275	Remote Similarity	NPD7521	Approved
0.6275	Remote Similarity	NPD7146	Approved
0.6275	Remote Similarity	NPD7334	Approved
0.6273	Remote Similarity	NPD5223	Approved
0.6271	Remote Similarity	NPD6274	Approved
0.6263	Remote Similarity	NPD1780	Approved
0.6263	Remote Similarity	NPD1779	Approved
0.6262	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD5328	Approved
0.624	Remote Similarity	NPD6033	Approved
0.6239	Remote Similarity	NPD4632	Approved
0.6238	Remote Similarity	NPD4786	Approved
0.6218	Remote Similarity	NPD6317	Approved
0.6218	Remote Similarity	NPD7115	Discovery
0.6216	Remote Similarity	NPD5225	Approved
0.6216	Remote Similarity	NPD5226	Approved
0.6216	Remote Similarity	NPD5211	Phase 2
0.6216	Remote Similarity	NPD5224	Approved
0.6216	Remote Similarity	NPD4633	Approved
0.6198	Remote Similarity	NPD8377	Approved
0.6198	Remote Similarity	NPD8294	Approved
0.6179	Remote Similarity	NPD6067	Discontinued
0.6168	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7900	Approved
0.6167	Remote Similarity	NPD6313	Approved
0.6167	Remote Similarity	NPD6314	Approved
0.6161	Remote Similarity	NPD5174	Approved
0.6161	Remote Similarity	NPD5175	Approved
0.6161	Remote Similarity	NPD4754	Approved
0.6148	Remote Similarity	NPD8296	Approved
0.6148	Remote Similarity	NPD6908	Approved
0.6148	Remote Similarity	NPD8380	Approved
0.6148	Remote Similarity	NPD8335	Approved
0.6148	Remote Similarity	NPD8379	Approved
0.6148	Remote Similarity	NPD8033	Approved
0.6148	Remote Similarity	NPD6909	Approved
0.6148	Remote Similarity	NPD8378	Approved
0.6132	Remote Similarity	NPD6079	Approved
0.6132	Remote Similarity	NPD5284	Approved
0.6132	Remote Similarity	NPD5281	Approved
0.6117	Remote Similarity	NPD6098	Approved
0.6106	Remote Similarity	NPD5141	Approved
0.6095	Remote Similarity	NPD6904	Approved
0.6095	Remote Similarity	NPD6673	Approved
0.6095	Remote Similarity	NPD6080	Approved
0.6095	Remote Similarity	NPD4753	Phase 2
0.6087	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3666	Approved
0.6066	Remote Similarity	NPD6319	Approved
0.6055	Remote Similarity	NPD4697	Phase 3
0.6053	Remote Similarity	NPD4768	Approved
0.6053	Remote Similarity	NPD4767	Approved
0.6053	Remote Similarity	NPD6920	Discontinued
0.6044	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3667	Approved
0.6038	Remote Similarity	NPD5207	Approved
0.6034	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6672	Approved
0.5983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4629	Approved
0.5963	Remote Similarity	NPD5210	Approved
0.5962	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6336	Discontinued
0.5948	Remote Similarity	NPD5128	Approved
0.5948	Remote Similarity	NPD4730	Approved
0.5948	Remote Similarity	NPD4729	Approved
0.5909	Remote Similarity	NPD5221	Approved
0.5909	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5222	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