NPASS Compound

Structure

NPC39370 OpenBabel07101719152D 33 38 0 0 0 0 0 0 0 0999 V2000 -4.2038 3.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1254 -0.5387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5927 -1.8555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8052 -1.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4588 -1.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7007 -0.0269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7267 -1.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9962 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4588 -0.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 0.3799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 -2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4271 -3.7192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 -2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7267 -0.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 0.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5927 0.1445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8025 2.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3903 1.2271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3848 1.1226 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4052 -3.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2093 2.9497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1473 -0.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 19 2 0 0 0 0 8 20 2 0 0 0 0 9 23 2 0 0 0 0 10 24 2 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 25 2 0 0 0 0 14 18 1 0 0 0 0 14 26 2 0 0 0 0 15 17 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 31 2 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 27 2 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 26 33 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.16
Volume:	455.596
LogP:	5.9
LogD:	4.343
LogS:	-7.295
# Rotatable Bonds:	5
TPSA:	56.25
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	2.524
Fsp3:	0.107
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.281
MDCK Permeability:	1.98584129975643e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.556
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	96.42008209228516%
Volume Distribution (VD):	0.551
Pgp-substrate:	1.172374963760376%

ADMET: Metabolism

CYP1A2-inhibitor:	0.918
CYP1A2-substrate:	0.869
CYP2C19-inhibitor:	0.972
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.935
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.801
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.815
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	5.608
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.773
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.462
Carcinogencity:	0.926
Eye Corrosion:	0.003
Eye Irritation:	0.563
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC39370

Natural Product ID:	NPC39370
*Common Name:**	KFJHFCIOEPNXMD-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KFJHFCIOEPNXMD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H22N2O3/c1-32-25-13-17(11-21-19-7-3-5-9-23(19)29-27(21)25)15-30-24-10-6-4-8-20(24)22-12-18(16-31)14-26(33-2)28(22)30/h3-14,16,29H,15H2,1-2H3
SMILES:	COc1cc(cc2c3ccccc3[nH]c12)Cn1c2ccccc2c2cc(cc(c12)OC)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633087
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO33199	murraya tetramera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26327273]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	38500.0	nM	PMID[448263]

☑ 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 NPC39370 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	586
0.1-0.2	3478
0.2-0.3	13402
0.3-0.4	5407
0.4-0.5	14528
0.5-0.6	3002
0.6-0.7	1763
0.7-0.8	485
0.8-0.85	33
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC473186
0.9082	High Similarity	NPC94157
0.9034	High Similarity	NPC187501
0.8873	High Similarity	NPC225279
0.8873	High Similarity	NPC132642
0.8826	High Similarity	NPC208084
0.8768	High Similarity	NPC39500
0.8618	High Similarity	NPC144452
0.8612	High Similarity	NPC45190
0.8605	High Similarity	NPC184408
0.8545	High Similarity	NPC473185
0.8539	High Similarity	NPC179287
0.8514	High Similarity	NPC474688
0.8451	Intermediate Similarity	NPC199667
0.843	Intermediate Similarity	NPC475253
0.8423	Intermediate Similarity	NPC274640
0.8404	Intermediate Similarity	NPC473181
0.8372	Intermediate Similarity	NPC473180
0.8349	Intermediate Similarity	NPC300156
0.8326	Intermediate Similarity	NPC294375
0.831	Intermediate Similarity	NPC283117
0.831	Intermediate Similarity	NPC249583
0.8295	Intermediate Similarity	NPC118228
0.8248	Intermediate Similarity	NPC473188
0.8246	Intermediate Similarity	NPC473183
0.8227	Intermediate Similarity	NPC473179
0.8219	Intermediate Similarity	NPC293151
0.8217	Intermediate Similarity	NPC475844
0.8202	Intermediate Similarity	NPC473187
0.8182	Intermediate Similarity	NPC46561
0.817	Intermediate Similarity	NPC470018
0.8161	Intermediate Similarity	NPC51388
0.8158	Intermediate Similarity	NPC473184
0.8119	Intermediate Similarity	NPC308137
0.8119	Intermediate Similarity	NPC310211
0.8114	Intermediate Similarity	NPC329631
0.8109	Intermediate Similarity	NPC53534
0.8072	Intermediate Similarity	NPC198503
0.8072	Intermediate Similarity	NPC280799
0.807	Intermediate Similarity	NPC49547
0.8068	Intermediate Similarity	NPC242928
0.8058	Intermediate Similarity	NPC152620
0.8056	Intermediate Similarity	NPC4687
0.8027	Intermediate Similarity	NPC150239
0.8026	Intermediate Similarity	NPC474701
0.7981	Intermediate Similarity	NPC128823
0.7974	Intermediate Similarity	NPC74575
0.7974	Intermediate Similarity	NPC257851
0.7957	Intermediate Similarity	NPC208522
0.7945	Intermediate Similarity	NPC471304
0.7937	Intermediate Similarity	NPC247803
0.7934	Intermediate Similarity	NPC89549
0.7931	Intermediate Similarity	NPC15801
0.7917	Intermediate Similarity	NPC475774
0.7909	Intermediate Similarity	NPC87413
0.7909	Intermediate Similarity	NPC9894
0.7895	Intermediate Similarity	NPC478078
0.7867	Intermediate Similarity	NPC472099
0.7857	Intermediate Similarity	NPC96321
0.7835	Intermediate Similarity	NPC469554
0.7817	Intermediate Similarity	NPC157931
0.7812	Intermediate Similarity	NPC169402
0.7808	Intermediate Similarity	NPC321428
0.7803	Intermediate Similarity	NPC116238
0.7802	Intermediate Similarity	NPC473182
0.7788	Intermediate Similarity	NPC477533
0.7783	Intermediate Similarity	NPC194740
0.7778	Intermediate Similarity	NPC474798
0.7778	Intermediate Similarity	NPC6786
0.7754	Intermediate Similarity	NPC477066
0.7737	Intermediate Similarity	NPC478083
0.7735	Intermediate Similarity	NPC470017
0.7722	Intermediate Similarity	NPC478081
0.7714	Intermediate Similarity	NPC160381
0.7713	Intermediate Similarity	NPC472098
0.7699	Intermediate Similarity	NPC303658
0.7692	Intermediate Similarity	NPC39679
0.7689	Intermediate Similarity	NPC152768
0.7689	Intermediate Similarity	NPC148183
0.7689	Intermediate Similarity	NPC36405
0.7682	Intermediate Similarity	NPC101543
0.7676	Intermediate Similarity	NPC26543
0.7669	Intermediate Similarity	NPC101350
0.7668	Intermediate Similarity	NPC208284
0.7668	Intermediate Similarity	NPC23294
0.7664	Intermediate Similarity	NPC475190
0.7655	Intermediate Similarity	NPC305984
0.7647	Intermediate Similarity	NPC478082
0.7647	Intermediate Similarity	NPC477067
0.7639	Intermediate Similarity	NPC477112
0.7636	Intermediate Similarity	NPC470930
0.7634	Intermediate Similarity	NPC264176
0.7632	Intermediate Similarity	NPC323969
0.7632	Intermediate Similarity	NPC174760
0.7629	Intermediate Similarity	NPC314954
0.7627	Intermediate Similarity	NPC235685
0.7625	Intermediate Similarity	NPC475666
0.7623	Intermediate Similarity	NPC303951
0.7623	Intermediate Similarity	NPC470020
0.7621	Intermediate Similarity	NPC473041
0.7619	Intermediate Similarity	NPC202503
0.7607	Intermediate Similarity	NPC196718
0.7605	Intermediate Similarity	NPC148889
0.7593	Intermediate Similarity	NPC17437
0.7591	Intermediate Similarity	NPC245816
0.7591	Intermediate Similarity	NPC476138
0.7589	Intermediate Similarity	NPC146418
0.7588	Intermediate Similarity	NPC288987
0.7583	Intermediate Similarity	NPC81939
0.7583	Intermediate Similarity	NPC473189
0.7582	Intermediate Similarity	NPC329982
0.7574	Intermediate Similarity	NPC180504
0.7573	Intermediate Similarity	NPC473540
0.7562	Intermediate Similarity	NPC270515
0.7556	Intermediate Similarity	NPC26679
0.7555	Intermediate Similarity	NPC276657
0.7554	Intermediate Similarity	NPC311906
0.7554	Intermediate Similarity	NPC471762
0.7553	Intermediate Similarity	NPC470022
0.755	Intermediate Similarity	NPC132385
0.7544	Intermediate Similarity	NPC131885
0.7542	Intermediate Similarity	NPC253675
0.7534	Intermediate Similarity	NPC210828
0.7534	Intermediate Similarity	NPC329793
0.7534	Intermediate Similarity	NPC86834
0.7532	Intermediate Similarity	NPC102593
0.7532	Intermediate Similarity	NPC474192
0.7532	Intermediate Similarity	NPC475720
0.75	Intermediate Similarity	NPC472285
0.75	Intermediate Similarity	NPC21638
0.75	Intermediate Similarity	NPC67401
0.75	Intermediate Similarity	NPC191489
0.749	Intermediate Similarity	NPC258048
0.7489	Intermediate Similarity	NPC260434
0.7488	Intermediate Similarity	NPC176127
0.748	Intermediate Similarity	NPC478080
0.7479	Intermediate Similarity	NPC184680
0.7469	Intermediate Similarity	NPC142385
0.7468	Intermediate Similarity	NPC227908
0.7465	Intermediate Similarity	NPC131017
0.7456	Intermediate Similarity	NPC170114
0.7456	Intermediate Similarity	NPC3207
0.7448	Intermediate Similarity	NPC470785
0.7446	Intermediate Similarity	NPC477532
0.7445	Intermediate Similarity	NPC476287
0.7432	Intermediate Similarity	NPC162484
0.743	Intermediate Similarity	NPC185197
0.7422	Intermediate Similarity	NPC185782
0.7417	Intermediate Similarity	NPC475816
0.7414	Intermediate Similarity	NPC216612
0.7412	Intermediate Similarity	NPC470549
0.7411	Intermediate Similarity	NPC53344
0.7407	Intermediate Similarity	NPC92111
0.7404	Intermediate Similarity	NPC252251
0.7404	Intermediate Similarity	NPC66777
0.7401	Intermediate Similarity	NPC118940
0.7399	Intermediate Similarity	NPC285558
0.7388	Intermediate Similarity	NPC165964
0.7382	Intermediate Similarity	NPC122436
0.7381	Intermediate Similarity	NPC100734
0.7381	Intermediate Similarity	NPC315634
0.7381	Intermediate Similarity	NPC88923
0.738	Intermediate Similarity	NPC469928
0.7377	Intermediate Similarity	NPC107836
0.7376	Intermediate Similarity	NPC329747
0.7375	Intermediate Similarity	NPC470784
0.7368	Intermediate Similarity	NPC469592
0.7368	Intermediate Similarity	NPC471080
0.7364	Intermediate Similarity	NPC72211
0.7361	Intermediate Similarity	NPC76748
0.7355	Intermediate Similarity	NPC72905
0.7354	Intermediate Similarity	NPC223427
0.7347	Intermediate Similarity	NPC63971
0.7347	Intermediate Similarity	NPC91868
0.7345	Intermediate Similarity	NPC209769
0.7342	Intermediate Similarity	NPC477531
0.7339	Intermediate Similarity	NPC307963
0.733	Intermediate Similarity	NPC74413
0.7326	Intermediate Similarity	NPC195788
0.7326	Intermediate Similarity	NPC237901
0.7325	Intermediate Similarity	NPC474428
0.7322	Intermediate Similarity	NPC316411
0.7321	Intermediate Similarity	NPC132539
0.732	Intermediate Similarity	NPC284685
0.7318	Intermediate Similarity	NPC243834
0.7318	Intermediate Similarity	NPC70956
0.7316	Intermediate Similarity	NPC264285
0.7315	Intermediate Similarity	NPC296527
0.7315	Intermediate Similarity	NPC471303
0.7311	Intermediate Similarity	NPC132329
0.7309	Intermediate Similarity	NPC260900
0.7308	Intermediate Similarity	NPC205372
0.7308	Intermediate Similarity	NPC322482
0.73	Intermediate Similarity	NPC209174
0.7297	Intermediate Similarity	NPC19872
0.7297	Intermediate Similarity	NPC176538
0.7296	Intermediate Similarity	NPC60621
0.7295	Intermediate Similarity	NPC78609
0.7293	Intermediate Similarity	NPC478074
0.7289	Intermediate Similarity	NPC472286

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 NPC39370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	669
0.2-0.3	909
0.3-0.4	1462
0.4-0.5	2810
0.5-0.6	2044
0.6-0.7	799
0.7-0.8	132
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8791	High Similarity	NPD6160	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD5479	Discontinued
0.8114	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD6242	Discontinued
0.8018	Intermediate Similarity	NPD4429	Discontinued
0.7888	Intermediate Similarity	NPD3006	Discontinued
0.7857	Intermediate Similarity	NPD5632	Approved
0.775	Intermediate Similarity	NPD5482	Discontinued
0.7749	Intermediate Similarity	NPD5022	Discontinued
0.7739	Intermediate Similarity	NPD7994	Phase 2
0.7712	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6456	Discontinued
0.7682	Intermediate Similarity	NPD3746	Discontinued
0.765	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD7395	Discontinued
0.7607	Intermediate Similarity	NPD4885	Approved
0.76	Intermediate Similarity	NPD3945	Discontinued
0.7597	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD8358	Approved
0.7573	Intermediate Similarity	NPD6716	Phase 1
0.7568	Intermediate Similarity	NPD7222	Phase 2
0.7566	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD6995	Phase 1
0.7564	Intermediate Similarity	NPD7688	Phase 1
0.7511	Intermediate Similarity	NPD7853	Phase 2
0.7511	Intermediate Similarity	NPD5416	Discontinued
0.75	Intermediate Similarity	NPD8363	Approved
0.75	Intermediate Similarity	NPD6530	Approved
0.75	Intermediate Similarity	NPD7708	Approved
0.75	Intermediate Similarity	NPD6531	Approved
0.75	Intermediate Similarity	NPD8364	Approved
0.7489	Intermediate Similarity	NPD7452	Approved
0.7489	Intermediate Similarity	NPD7453	Approved
0.7489	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4952	Phase 3
0.7441	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3257	Approved
0.7403	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5901	Discontinued
0.7386	Intermediate Similarity	NPD7417	Discontinued
0.7385	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7803	Approved
0.7381	Intermediate Similarity	NPD5450	Discontinued
0.7378	Intermediate Similarity	NPD5658	Approved
0.7368	Intermediate Similarity	NPD8463	Approved
0.7359	Intermediate Similarity	NPD3258	Approved
0.7353	Intermediate Similarity	NPD4373	Phase 2
0.7347	Intermediate Similarity	NPD4558	Phase 2
0.7339	Intermediate Similarity	NPD1038	Approved
0.7339	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD5903	Approved
0.7336	Intermediate Similarity	NPD5902	Approved
0.7333	Intermediate Similarity	NPD5429	Discontinued
0.7331	Intermediate Similarity	NPD5559	Phase 2
0.7328	Intermediate Similarity	NPD5850	Phase 3
0.7327	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5913	Phase 3
0.7326	Intermediate Similarity	NPD8465	Approved
0.7326	Intermediate Similarity	NPD8427	Approved
0.7326	Intermediate Similarity	NPD8429	Approved
0.7326	Intermediate Similarity	NPD8428	Approved
0.7326	Intermediate Similarity	NPD8466	Approved
0.7326	Intermediate Similarity	NPD8467	Approved
0.732	Intermediate Similarity	NPD7955	Approved
0.732	Intermediate Similarity	NPD7956	Approved
0.7314	Intermediate Similarity	NPD6790	Phase 1
0.7308	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4418	Discontinued
0.7289	Intermediate Similarity	NPD3003	Approved
0.7281	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD8459	Approved
0.728	Intermediate Similarity	NPD8460	Approved
0.7276	Intermediate Similarity	NPD8102	Discontinued
0.7265	Intermediate Similarity	NPD5488	Discontinued
0.7265	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5293	Phase 2
0.7257	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2951	Discontinued
0.7246	Intermediate Similarity	NPD7603	Discontinued
0.724	Intermediate Similarity	NPD6961	Discontinued
0.724	Intermediate Similarity	NPD5003	Discontinued
0.7237	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2510	Approved
0.7225	Intermediate Similarity	NPD2509	Approved
0.7215	Intermediate Similarity	NPD3259	Approved
0.7215	Intermediate Similarity	NPD4328	Approved
0.7214	Intermediate Similarity	NPD8426	Approved
0.7214	Intermediate Similarity	NPD8425	Approved
0.7212	Intermediate Similarity	NPD8403	Phase 1
0.7211	Intermediate Similarity	NPD8091	Phase 3
0.7205	Intermediate Similarity	NPD4502	Phase 2
0.72	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7924	Phase 2
0.7188	Intermediate Similarity	NPD7925	Phase 2
0.7179	Intermediate Similarity	NPD7180	Phase 3
0.7175	Intermediate Similarity	NPD3825	Phase 3
0.7168	Intermediate Similarity	NPD5426	Phase 3
0.7167	Intermediate Similarity	NPD6985	Discontinued
0.7155	Intermediate Similarity	NPD5612	Discontinued
0.7149	Intermediate Similarity	NPD7467	Discontinued
0.7149	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6517	Phase 3
0.7137	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD3875	Discontinued
0.7137	Intermediate Similarity	NPD3402	Phase 1
0.7137	Intermediate Similarity	NPD6770	Approved
0.7137	Intermediate Similarity	NPD7194	Discontinued
0.7137	Intermediate Similarity	NPD7001	Phase 3
0.713	Intermediate Similarity	NPD7470	Discontinued
0.7126	Intermediate Similarity	NPD8100	Phase 3
0.7122	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4368	Phase 2
0.7117	Intermediate Similarity	NPD5512	Phase 3
0.7108	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3986	Discontinued
0.7106	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5866	Approved
0.7097	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7096	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3947	Discontinued
0.7092	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD4442	Phase 2
0.7073	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7181	Phase 3
0.7064	Intermediate Similarity	NPD5256	Discontinued
0.7061	Intermediate Similarity	NPD8016	Phase 3
0.7061	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2565	Phase 2
0.7045	Intermediate Similarity	NPD2564	Approved
0.704	Intermediate Similarity	NPD8101	Phase 3
0.7025	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1768	Approved
0.7021	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7206	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7921	Approved
0.7013	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3392	Approved
0.7012	Intermediate Similarity	NPD1659	Phase 1
0.7012	Intermediate Similarity	NPD5924	Discontinued
0.7	Intermediate Similarity	NPD2916	Discontinued
0.7	Intermediate Similarity	NPD6376	Discontinued
0.6996	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7558	Phase 2
0.6991	Remote Similarity	NPD4501	Approved
0.6991	Remote Similarity	NPD484	Approved
0.6991	Remote Similarity	NPD4500	Approved
0.6987	Remote Similarity	NPD5530	Phase 1
0.6983	Remote Similarity	NPD6962	Phase 2
0.6983	Remote Similarity	NPD1867	Approved
0.697	Remote Similarity	NPD7872	Phase 2
0.6955	Remote Similarity	NPD4948	Discontinued
0.6951	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3354	Phase 2
0.6947	Remote Similarity	NPD8396	Approved
0.6947	Remote Similarity	NPD8395	Approved
0.6947	Remote Similarity	NPD2778	Approved
0.6943	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4454	Phase 2
0.6939	Remote Similarity	NPD5891	Approved
0.6936	Remote Similarity	NPD3389	Approved
0.6936	Remote Similarity	NPD3394	Approved
0.6936	Remote Similarity	NPD3393	Approved
0.6929	Remote Similarity	NPD4845	Discontinued
0.6926	Remote Similarity	NPD2189	Approved
0.6926	Remote Similarity	NPD2187	Approved
0.6923	Remote Similarity	NPD8489	Phase 1
0.692	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7659	Discontinued
0.6914	Remote Similarity	NPD1467	Approved
0.6914	Remote Similarity	NPD1466	Phase 3
0.691	Remote Similarity	NPD5939	Approved
0.691	Remote Similarity	NPD5066	Phase 2
0.691	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5936	Approved
0.691	Remote Similarity	NPD5067	Phase 2
0.69	Remote Similarity	NPD8349	Phase 1
0.69	Remote Similarity	NPD6176	Phase 1
0.6899	Remote Similarity	NPD5399	Discovery
0.6895	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7766	Phase 2
0.689	Remote Similarity	NPD5532	Phase 2
0.6889	Remote Similarity	NPD6550	Discontinued
0.6888	Remote Similarity	NPD7426	Phase 1
0.6883	Remote Similarity	NPD1392	Approved
0.6872	Remote Similarity	NPD6999	Discontinued
0.6872	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6138	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