NPASS Compound

Structure

NPC472238 OpenBabel07101719512D 36 41 0 0 1 0 0 0 0 0999 V2000 2.1083 1.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5893 -3.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7267 -3.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9009 -4.3998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3710 -1.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9760 -1.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4123 -2.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9009 -1.7948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9474 -1.7948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0277 -0.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9227 -2.4754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6312 -3.1134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1209 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3094 -4.1549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9068 0.6588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9068 -1.2481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8136 0.9535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.5428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9474 -3.4463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3777 -2.6206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4384 -3.7671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3741 0.1821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7363 -1.8861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9009 -3.4463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4707 -2.6206 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0277 -1.2481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1209 -1.5428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9068 -0.2946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5381 -2.8188 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5604 -0.7714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3312 -2.6206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6126 -4.2438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3276 0.1821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5499 -1.2969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8136 -0.5893 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 18 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 27 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 25 1 0 0 0 0 10 13 1 0 0 0 0 10 26 1 0 0 0 0 11 12 1 0 0 0 0 11 27 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 1 1 1 0 0 0 17 22 1 0 0 0 0 18 30 1 1 0 0 0 19 24 1 0 0 0 0 19 25 1 1 0 0 0 20 24 1 0 0 0 0 20 31 2 0 0 0 0 21 29 1 1 0 0 0 21 32 1 0 0 0 0 22 33 2 0 0 0 0 22 35 1 0 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 23 34 2 0 0 0 0 25 29 1 6 0 0 0 26 27 1 1 0 0 0 27 30 1 1 0 0 0 28 15 1 1 0 0 0 28 35 1 0 0 0 0 28 36 1 0 0 0 0 29 12 1 6 0 0 0 30 13 1 1 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	520.929
LogP:	2.926
LogD:	2.953
LogS:	-4.793
# Rotatable Bonds:	0
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.471
Synthetic Accessibility Score:	6.474
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.206
MDCK Permeability:	2.076018245134037e-05
Pgp-inhibitor:	0.865
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.533

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	80.2970199584961%
Volume Distribution (VD):	0.872
Pgp-substrate:	15.905962944030762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	9.648
Half-life (T1/2):	0.481

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.294
Carcinogencity:	0.886
Eye Corrosion:	0.004
Eye Irritation:	0.055
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC472238

Natural Product ID:	NPC472238
*Common Name:**	AFAQACTXQLSZEJ-UEBGPECHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AFAQACTXQLSZEJ-UEBGPECHSA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-17-15-28(35-22(17)33)16-18(2)30(36-28)13-10-26(6)23(34)29(12-11-27(26,30)7)21(32)14-19-24(3,4)20(31)8-9-25(19,29)5/h17-19,21,32H,8-16H2,1-7H3/t17-,18-,19+,21+,25+,26+,27+,28+,29-,30-/m1/s1
SMILES:	CC1CC2(CC(C3(O2)CCC4(C3(CCC5(C4=O)C(CC6C5(CCC(=O)C6(C)C)C)O)C)C)C)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353855
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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	=	15400.0	nM	PMID[544170]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	10100.0	nM	PMID[544170]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12300.0	nM	PMID[544170]
NPT27	Others	Unspecified		IC50	=	8200.0	nM	PMID[544170]

☑ 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 NPC472238 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	429
0.1-0.2	4152
0.2-0.3	12426
0.3-0.4	11093
0.4-0.5	6655
0.5-0.6	6287
0.6-0.7	1465
0.7-0.8	177
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472237
0.8667	High Similarity	NPC33398
0.8495	Intermediate Similarity	NPC472231
0.8495	Intermediate Similarity	NPC472232
0.8367	Intermediate Similarity	NPC244969
0.8367	Intermediate Similarity	NPC213528
0.8295	Intermediate Similarity	NPC472229
0.8295	Intermediate Similarity	NPC472230
0.82	Intermediate Similarity	NPC100078
0.8119	Intermediate Similarity	NPC306776
0.8119	Intermediate Similarity	NPC166079
0.8111	Intermediate Similarity	NPC472847
0.8105	Intermediate Similarity	NPC161035
0.8021	Intermediate Similarity	NPC470424
0.8021	Intermediate Similarity	NPC206878
0.8	Intermediate Similarity	NPC474065
0.7979	Intermediate Similarity	NPC472234
0.7979	Intermediate Similarity	NPC472233
0.7979	Intermediate Similarity	NPC200580
0.7917	Intermediate Similarity	NPC476189
0.7912	Intermediate Similarity	NPC157328
0.79	Intermediate Similarity	NPC178853
0.7857	Intermediate Similarity	NPC476728
0.7857	Intermediate Similarity	NPC193785
0.7843	Intermediate Similarity	NPC88469
0.7802	Intermediate Similarity	NPC477935
0.7778	Intermediate Similarity	NPC475490
0.7755	Intermediate Similarity	NPC305808
0.7692	Intermediate Similarity	NPC58631
0.7685	Intermediate Similarity	NPC79193
0.7677	Intermediate Similarity	NPC116683
0.767	Intermediate Similarity	NPC473526
0.767	Intermediate Similarity	NPC472227
0.767	Intermediate Similarity	NPC473701
0.767	Intermediate Similarity	NPC472228
0.7667	Intermediate Similarity	NPC472310
0.766	Intermediate Similarity	NPC92139
0.7653	Intermediate Similarity	NPC470423
0.7647	Intermediate Similarity	NPC470172
0.764	Intermediate Similarity	NPC477918
0.7634	Intermediate Similarity	NPC25802
0.7634	Intermediate Similarity	NPC101138
0.7634	Intermediate Similarity	NPC51135
0.7634	Intermediate Similarity	NPC477434
0.7634	Intermediate Similarity	NPC82492
0.7629	Intermediate Similarity	NPC475878
0.7609	Intermediate Similarity	NPC100366
0.7609	Intermediate Similarity	NPC242771
0.7609	Intermediate Similarity	NPC164289
0.7609	Intermediate Similarity	NPC311642
0.7609	Intermediate Similarity	NPC477936
0.7604	Intermediate Similarity	NPC61688
0.7582	Intermediate Similarity	NPC1882
0.7582	Intermediate Similarity	NPC472853
0.7573	Intermediate Similarity	NPC471253
0.7573	Intermediate Similarity	NPC473406
0.7556	Intermediate Similarity	NPC185465
0.7556	Intermediate Similarity	NPC476732
0.7556	Intermediate Similarity	NPC199965
0.7553	Intermediate Similarity	NPC473350
0.7528	Intermediate Similarity	NPC477932
0.7528	Intermediate Similarity	NPC477933
0.7527	Intermediate Similarity	NPC217559
0.7527	Intermediate Similarity	NPC268578
0.7527	Intermediate Similarity	NPC292458
0.7524	Intermediate Similarity	NPC176756
0.7523	Intermediate Similarity	NPC470116
0.7523	Intermediate Similarity	NPC470115
0.75	Intermediate Similarity	NPC477614
0.75	Intermediate Similarity	NPC226491
0.75	Intermediate Similarity	NPC471221
0.7477	Intermediate Similarity	NPC98633
0.7474	Intermediate Similarity	NPC472272
0.7473	Intermediate Similarity	NPC474754
0.7473	Intermediate Similarity	NPC320144
0.7453	Intermediate Similarity	NPC167044
0.7449	Intermediate Similarity	NPC150383
0.7449	Intermediate Similarity	NPC52756
0.7447	Intermediate Similarity	NPC471044
0.7447	Intermediate Similarity	NPC473336
0.7444	Intermediate Similarity	NPC477919
0.7444	Intermediate Similarity	NPC169389
0.7444	Intermediate Similarity	NPC474404
0.7444	Intermediate Similarity	NPC180199
0.7431	Intermediate Similarity	NPC285086
0.7423	Intermediate Similarity	NPC471459
0.7423	Intermediate Similarity	NPC477440
0.7423	Intermediate Similarity	NPC477443
0.7423	Intermediate Similarity	NPC67653
0.7419	Intermediate Similarity	NPC13494
0.7419	Intermediate Similarity	NPC317066
0.7419	Intermediate Similarity	NPC102156
0.7419	Intermediate Similarity	NPC61107
0.7419	Intermediate Similarity	NPC148740
0.7419	Intermediate Similarity	NPC24556
0.7419	Intermediate Similarity	NPC289486
0.7416	Intermediate Similarity	NPC179922
0.7416	Intermediate Similarity	NPC477934
0.7416	Intermediate Similarity	NPC132064
0.7407	Intermediate Similarity	NPC473062
0.74	Intermediate Similarity	NPC215570
0.74	Intermediate Similarity	NPC62407
0.74	Intermediate Similarity	NPC21897
0.74	Intermediate Similarity	NPC287354
0.7396	Intermediate Similarity	NPC239938
0.7383	Intermediate Similarity	NPC217041
0.7379	Intermediate Similarity	NPC478181
0.7374	Intermediate Similarity	NPC256104
0.7374	Intermediate Similarity	NPC182740
0.7374	Intermediate Similarity	NPC211845
0.7374	Intermediate Similarity	NPC122083
0.7374	Intermediate Similarity	NPC228700
0.7353	Intermediate Similarity	NPC253995
0.7347	Intermediate Similarity	NPC477442
0.7347	Intermediate Similarity	NPC477444
0.7347	Intermediate Similarity	NPC477433
0.7347	Intermediate Similarity	NPC77756
0.734	Intermediate Similarity	NPC327451
0.734	Intermediate Similarity	NPC259173
0.7333	Intermediate Similarity	NPC114365
0.7333	Intermediate Similarity	NPC18044
0.7333	Intermediate Similarity	NPC154962
0.7333	Intermediate Similarity	NPC470167
0.7333	Intermediate Similarity	NPC327093
0.7333	Intermediate Similarity	NPC177518
0.7333	Intermediate Similarity	NPC123070
0.7333	Intermediate Similarity	NPC169089
0.7333	Intermediate Similarity	NPC132304
0.7333	Intermediate Similarity	NPC88890
0.7333	Intermediate Similarity	NPC18433
0.7333	Intermediate Similarity	NPC471046
0.7327	Intermediate Similarity	NPC475785
0.7327	Intermediate Similarity	NPC475765
0.732	Intermediate Similarity	NPC221993
0.732	Intermediate Similarity	NPC211162
0.732	Intermediate Similarity	NPC183374
0.7315	Intermediate Similarity	NPC49730
0.7315	Intermediate Similarity	NPC98069
0.7315	Intermediate Similarity	NPC182185
0.7308	Intermediate Similarity	NPC471254
0.7303	Intermediate Similarity	NPC477930
0.73	Intermediate Similarity	NPC472223
0.73	Intermediate Similarity	NPC472224
0.7292	Intermediate Similarity	NPC474448
0.7292	Intermediate Similarity	NPC80700
0.7282	Intermediate Similarity	NPC108371
0.7273	Intermediate Similarity	NPC469940
0.7273	Intermediate Similarity	NPC97002
0.7273	Intermediate Similarity	NPC197701
0.7264	Intermediate Similarity	NPC103172
0.7264	Intermediate Similarity	NPC164600
0.7264	Intermediate Similarity	NPC215408
0.7264	Intermediate Similarity	NPC168890
0.7263	Intermediate Similarity	NPC291310
0.7263	Intermediate Similarity	NPC50438
0.7263	Intermediate Similarity	NPC319909
0.7255	Intermediate Similarity	NPC470632
0.7255	Intermediate Similarity	NPC328180
0.7255	Intermediate Similarity	NPC471241
0.7255	Intermediate Similarity	NPC74466
0.7255	Intermediate Similarity	NPC278028
0.7253	Intermediate Similarity	NPC207010
0.7253	Intermediate Similarity	NPC471151
0.7253	Intermediate Similarity	NPC317913
0.7253	Intermediate Similarity	NPC307865
0.7248	Intermediate Similarity	NPC469824
0.7248	Intermediate Similarity	NPC471251
0.7245	Intermediate Similarity	NPC24772
0.7245	Intermediate Similarity	NPC116146
0.7238	Intermediate Similarity	NPC140723
0.7238	Intermediate Similarity	NPC107385
0.7232	Intermediate Similarity	NPC179429
0.7228	Intermediate Similarity	NPC470031
0.7222	Intermediate Similarity	NPC155441
0.7222	Intermediate Similarity	NPC472311
0.7222	Intermediate Similarity	NPC125767
0.7222	Intermediate Similarity	NPC35871
0.7222	Intermediate Similarity	NPC179858
0.7222	Intermediate Similarity	NPC21220
0.7222	Intermediate Similarity	NPC471250
0.7222	Intermediate Similarity	NPC68565
0.7216	Intermediate Similarity	NPC252714
0.7216	Intermediate Similarity	NPC134197
0.7212	Intermediate Similarity	NPC39683
0.7204	Intermediate Similarity	NPC134227
0.72	Intermediate Similarity	NPC472226
0.72	Intermediate Similarity	NPC472225
0.7196	Intermediate Similarity	NPC290247
0.7196	Intermediate Similarity	NPC469788
0.7196	Intermediate Similarity	NPC469787
0.7191	Intermediate Similarity	NPC310766
0.7191	Intermediate Similarity	NPC248567
0.7191	Intermediate Similarity	NPC474755
0.7184	Intermediate Similarity	NPC292775
0.7184	Intermediate Similarity	NPC472144
0.7184	Intermediate Similarity	NPC211087
0.7182	Intermediate Similarity	NPC98870
0.7174	Intermediate Similarity	NPC471045
0.7159	Intermediate Similarity	NPC477929
0.7156	Intermediate Similarity	NPC106760

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 NPC472238 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	466
0.1-0.2	3928
0.2-0.3	3335
0.3-0.4	821
0.4-0.5	274
0.5-0.6	231
0.6-0.7	90
0.7-0.8	5
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
0.7614	Intermediate Similarity	NPD3702	Approved
0.7333	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5777	Approved
0.7253	Intermediate Similarity	NPD6116	Phase 1
0.7212	Intermediate Similarity	NPD1700	Approved
0.717	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4245	Approved
0.7159	Intermediate Similarity	NPD4244	Approved
0.7143	Intermediate Similarity	NPD6117	Approved
0.7111	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3698	Phase 2
0.6989	Remote Similarity	NPD4802	Phase 2
0.6989	Remote Similarity	NPD6115	Approved
0.6989	Remote Similarity	NPD4238	Approved
0.6989	Remote Similarity	NPD6697	Approved
0.6989	Remote Similarity	NPD6118	Approved
0.6989	Remote Similarity	NPD6114	Approved
0.6977	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7078	Approved
0.6972	Remote Similarity	NPD7320	Approved
0.6889	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6081	Approved
0.6875	Remote Similarity	NPD6882	Approved
0.6842	Remote Similarity	NPD6928	Phase 2
0.6807	Remote Similarity	NPD7492	Approved
0.6789	Remote Similarity	NPD5739	Approved
0.6789	Remote Similarity	NPD6675	Approved
0.6789	Remote Similarity	NPD7128	Approved
0.6789	Remote Similarity	NPD6402	Approved
0.6778	Remote Similarity	NPD4789	Approved
0.6757	Remote Similarity	NPD6372	Approved
0.6757	Remote Similarity	NPD6373	Approved
0.6752	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.6705	Remote Similarity	NPD4224	Phase 2
0.6699	Remote Similarity	NPD6399	Phase 3
0.6694	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD3703	Phase 2
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6637	Remote Similarity	NPD6649	Approved
0.6637	Remote Similarity	NPD6650	Approved
0.6604	Remote Similarity	NPD6084	Phase 2
0.6604	Remote Similarity	NPD6083	Phase 2
0.6602	Remote Similarity	NPD8034	Phase 2
0.6602	Remote Similarity	NPD8035	Phase 2
0.6577	Remote Similarity	NPD5697	Approved
0.6577	Remote Similarity	NPD5701	Approved
0.6556	Remote Similarity	NPD5360	Phase 3
0.6556	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6016	Approved
0.6555	Remote Similarity	NPD6015	Approved
0.6549	Remote Similarity	NPD6883	Approved
0.6549	Remote Similarity	NPD7102	Approved
0.6549	Remote Similarity	NPD7290	Approved
0.6518	Remote Similarity	NPD6011	Approved
0.65	Remote Similarity	NPD5988	Approved
0.6491	Remote Similarity	NPD8130	Phase 1
0.6491	Remote Similarity	NPD6617	Approved
0.6491	Remote Similarity	NPD6847	Approved
0.6491	Remote Similarity	NPD6869	Approved
0.6491	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6008	Approved
0.6471	Remote Similarity	NPD6903	Approved
0.6465	Remote Similarity	NPD4788	Approved
0.646	Remote Similarity	NPD6013	Approved
0.646	Remote Similarity	NPD6014	Approved
0.646	Remote Similarity	NPD6012	Approved
0.6435	Remote Similarity	NPD8297	Approved
0.6415	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3198	Approved
0.6389	Remote Similarity	NPD5696	Approved
0.6374	Remote Similarity	NPD229	Approved
0.6371	Remote Similarity	NPD6033	Approved
0.6356	Remote Similarity	NPD6009	Approved
0.6337	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7319	Approved
0.6296	Remote Similarity	NPD4755	Approved
0.6283	Remote Similarity	NPD6412	Phase 2
0.6281	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6409	Approved
0.6275	Remote Similarity	NPD5330	Approved
0.6275	Remote Similarity	NPD7146	Approved
0.6275	Remote Similarity	NPD7521	Approved
0.6275	Remote Similarity	NPD6684	Approved
0.6275	Remote Similarity	NPD7334	Approved
0.6263	Remote Similarity	NPD5369	Approved
0.6262	Remote Similarity	NPD5695	Phase 3
0.6228	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD8171	Discontinued
0.621	Remote Similarity	NPD7507	Approved
0.62	Remote Similarity	NPD6435	Approved
0.6198	Remote Similarity	NPD6319	Approved
0.6182	Remote Similarity	NPD5286	Approved
0.6182	Remote Similarity	NPD5285	Approved
0.6182	Remote Similarity	NPD4700	Approved
0.6182	Remote Similarity	NPD4696	Approved
0.617	Remote Similarity	NPD4758	Discontinued
0.6167	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6274	Approved
0.6132	Remote Similarity	NPD5284	Approved
0.6132	Remote Similarity	NPD5281	Approved
0.6126	Remote Similarity	NPD5223	Approved
0.6122	Remote Similarity	NPD3671	Phase 1
0.6122	Remote Similarity	NPD5364	Discontinued
0.6117	Remote Similarity	NPD6098	Approved
0.6117	Remote Similarity	NPD5786	Approved
0.6116	Remote Similarity	NPD7100	Approved
0.6116	Remote Similarity	NPD7101	Approved
0.6102	Remote Similarity	NPD8133	Approved
0.6102	Remote Similarity	NPD4632	Approved
0.6095	Remote Similarity	NPD5328	Approved
0.6095	Remote Similarity	NPD6904	Approved
0.6095	Remote Similarity	NPD6080	Approved
0.6095	Remote Similarity	NPD6673	Approved
0.6095	Remote Similarity	NPD4753	Phase 2
0.6083	Remote Similarity	NPD6317	Approved
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD4786	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3666	Approved
0.6075	Remote Similarity	NPD4202	Approved
0.6071	Remote Similarity	NPD5211	Phase 2
0.6071	Remote Similarity	NPD4633	Approved
0.6071	Remote Similarity	NPD5225	Approved
0.6071	Remote Similarity	NPD5224	Approved
0.6071	Remote Similarity	NPD5226	Approved
0.6064	Remote Similarity	NPD4787	Phase 1
0.6044	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5207	Approved
0.6033	Remote Similarity	NPD6314	Approved
0.6033	Remote Similarity	NPD6313	Approved
0.6019	Remote Similarity	NPD6001	Approved
0.6018	Remote Similarity	NPD5174	Approved
0.6018	Remote Similarity	NPD5175	Approved
0.6018	Remote Similarity	NPD4754	Approved
0.6017	Remote Similarity	NPD6053	Discontinued
0.6016	Remote Similarity	NPD6909	Approved
0.6016	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6672	Approved
0.5983	Remote Similarity	NPD4634	Approved
0.5981	Remote Similarity	NPD6079	Approved
0.5965	Remote Similarity	NPD5141	Approved
0.5963	Remote Similarity	NPD5210	Approved
0.5963	Remote Similarity	NPD7991	Discontinued
0.5963	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.595	Remote Similarity	NPD7115	Discovery
0.595	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD1780	Approved
0.5941	Remote Similarity	NPD1779	Approved
0.592	Remote Similarity	NPD7604	Phase 2
0.592	Remote Similarity	NPD7122	Discontinued
0.5913	Remote Similarity	NPD4767	Approved
0.5913	Remote Similarity	NPD4768	Approved
0.5909	Remote Similarity	NPD4697	Phase 3
0.5897	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD5956	Approved
0.5888	Remote Similarity	NPD5785	Approved
0.5887	Remote Similarity	NPD5983	Phase 2
0.5882	Remote Similarity	NPD4269	Approved
0.5882	Remote Similarity	NPD4221	Approved
0.5882	Remote Similarity	NPD4223	Phase 3
0.5882	Remote Similarity	NPD3667	Approved
0.5882	Remote Similarity	NPD4270	Approved
0.5877	Remote Similarity	NPD6052	Approved
0.5868	Remote Similarity	NPD6940	Discontinued
0.5865	Remote Similarity	NPD5329	Approved
0.5856	Remote Similarity	NPD7902	Approved
0.5854	Remote Similarity	NPD7519	Approved
0.5854	Remote Similarity	NPD7517	Approved
0.5854	Remote Similarity	NPD7518	Approved
0.5849	Remote Similarity	NPD5208	Approved
0.5833	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD6050	Approved
0.5833	Remote Similarity	NPD5693	Phase 1
0.5827	Remote Similarity	NPD6336	Discontinued
0.5825	Remote Similarity	NPD3669	Approved
0.5825	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD4730	Approved
0.5812	Remote Similarity	NPD5128	Approved
0.5812	Remote Similarity	NPD4729	Approved
0.581	Remote Similarity	NPD3618	Phase 1
0.5804	Remote Similarity	NPD7638	Approved
0.5794	Remote Similarity	NPD8328	Phase 3
0.5794	Remote Similarity	NPD6067	Discontinued
0.5789	Remote Similarity	NPD8138	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