NPASS Compound

Structure

NPC132642 OpenBabel07101718182D 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 1 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:	436.18
Volume:	458.232
LogP:	5.645
LogD:	4.094
LogS:	-7.018
# Rotatable Bonds:	5
TPSA:	59.41
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	2.48
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.259
MDCK Permeability:	2.0554152797558345e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.166
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	96.94598388671875%
Volume Distribution (VD):	0.671
Pgp-substrate:	1.1015805006027222%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.962
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.882
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.971
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.798
CYP3A4-substrate:	0.619

ADMET: Excretion

Clearance (CL):	7.091
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.868
AMES Toxicity:	0.856
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.307
Carcinogencity:	0.919
Eye Corrosion:	0.003
Eye Irritation:	0.177
Respiratory Toxicity:	0.688

Download Data

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

Natural Product: NPC132642

Natural Product ID:	NPC132642
*Common Name:**	Bismurrayafolinol
IUPAC Name:	[1-methoxy-9-[(1-methoxy-9H-carbazol-3-yl)methyl]carbazol-3-yl]methanol
Synonyms:
Standard InCHIKey:	ORBVDSSXNGYTRX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H24N2O3/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/h3-14,29,31H,15-16H2,1-2H3
SMILES:	COc1cc(cc2c3ccccc3[nH]c12)Cn1c2ccccc2c2cc(cc(c12)OC)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633086
PubChem CID:	23245461
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	=	19300.0	nM	PMID[525019]

☑ 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 NPC132642 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	500
0.1-0.2	3091
0.2-0.3	13969
0.3-0.4	7447
0.4-0.5	12288
0.5-0.6	3088
0.6-0.7	1814
0.7-0.8	456
0.8-0.85	27
0.85-0.9	12
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9641	High Similarity	NPC94157
0.9412	High Similarity	NPC473185
0.9069	High Similarity	NPC473179
0.9057	High Similarity	NPC473183
0.9026	High Similarity	NPC128823
0.8962	High Similarity	NPC473184
0.8955	High Similarity	NPC199667
0.891	High Similarity	NPC475253
0.8905	High Similarity	NPC473181
0.8873	High Similarity	NPC39370
0.8868	High Similarity	NPC473186
0.8867	High Similarity	NPC473180
0.8657	High Similarity	NPC475774
0.8565	High Similarity	NPC473182
0.8564	High Similarity	NPC242928
0.8458	Intermediate Similarity	NPC202503
0.831	Intermediate Similarity	NPC477533
0.8271	Intermediate Similarity	NPC477532
0.8265	Intermediate Similarity	NPC469554
0.8256	Intermediate Similarity	NPC474798
0.8211	Intermediate Similarity	NPC252251
0.8199	Intermediate Similarity	NPC469592
0.8199	Intermediate Similarity	NPC471080
0.8136	Intermediate Similarity	NPC477531
0.8131	Intermediate Similarity	NPC184408
0.8116	Intermediate Similarity	NPC223427
0.8104	Intermediate Similarity	NPC208284
0.81	Intermediate Similarity	NPC101543
0.8095	Intermediate Similarity	NPC209769
0.8091	Intermediate Similarity	NPC209174
0.8088	Intermediate Similarity	NPC70956
0.8088	Intermediate Similarity	NPC243834
0.8077	Intermediate Similarity	NPC470930
0.8047	Intermediate Similarity	NPC469594
0.8045	Intermediate Similarity	NPC314954
0.804	Intermediate Similarity	NPC473189
0.8039	Intermediate Similarity	NPC251090
0.8038	Intermediate Similarity	NPC476106
0.8029	Intermediate Similarity	NPC476138
0.8029	Intermediate Similarity	NPC245816
0.8	Intermediate Similarity	NPC193777
0.7982	Intermediate Similarity	NPC180504
0.7981	Intermediate Similarity	NPC26679
0.7971	Intermediate Similarity	NPC329793
0.7965	Intermediate Similarity	NPC473188
0.7962	Intermediate Similarity	NPC475910
0.7953	Intermediate Similarity	NPC8022
0.7953	Intermediate Similarity	NPC470799
0.7944	Intermediate Similarity	NPC478074
0.7944	Intermediate Similarity	NPC39500
0.7941	Intermediate Similarity	NPC307963
0.7941	Intermediate Similarity	NPC475190
0.794	Intermediate Similarity	NPC176127
0.7934	Intermediate Similarity	NPC187501
0.7925	Intermediate Similarity	NPC469589
0.7911	Intermediate Similarity	NPC473187
0.7902	Intermediate Similarity	NPC131017
0.7895	Intermediate Similarity	NPC291535
0.7895	Intermediate Similarity	NPC475112
0.7895	Intermediate Similarity	NPC475085
0.7887	Intermediate Similarity	NPC5145
0.7883	Intermediate Similarity	NPC274640
0.7879	Intermediate Similarity	NPC88363
0.7873	Intermediate Similarity	NPC227908
0.787	Intermediate Similarity	NPC170114
0.7857	Intermediate Similarity	NPC162484
0.7843	Intermediate Similarity	NPC92111
0.7841	Intermediate Similarity	NPC11408
0.784	Intermediate Similarity	NPC185782
0.7839	Intermediate Similarity	NPC478032
0.7837	Intermediate Similarity	NPC18487
0.7828	Intermediate Similarity	NPC179287
0.7826	Intermediate Similarity	NPC284141
0.7824	Intermediate Similarity	NPC470549
0.7824	Intermediate Similarity	NPC118228
0.782	Intermediate Similarity	NPC285558
0.7818	Intermediate Similarity	NPC144452
0.7814	Intermediate Similarity	NPC48353
0.7808	Intermediate Similarity	NPC225279
0.7804	Intermediate Similarity	NPC471304
0.7799	Intermediate Similarity	NPC249040
0.7799	Intermediate Similarity	NPC329747
0.7794	Intermediate Similarity	NPC76748
0.7788	Intermediate Similarity	NPC72211
0.7788	Intermediate Similarity	NPC477110
0.7783	Intermediate Similarity	NPC472111
0.7778	Intermediate Similarity	NPC266931
0.7773	Intermediate Similarity	NPC217554
0.7763	Intermediate Similarity	NPC213530
0.7763	Intermediate Similarity	NPC193267
0.7763	Intermediate Similarity	NPC208084
0.7759	Intermediate Similarity	NPC471891
0.7745	Intermediate Similarity	NPC246700
0.7745	Intermediate Similarity	NPC296527
0.7738	Intermediate Similarity	NPC280272
0.7733	Intermediate Similarity	NPC474688
0.7714	Intermediate Similarity	NPC176538
0.7714	Intermediate Similarity	NPC19872
0.771	Intermediate Similarity	NPC477111
0.7709	Intermediate Similarity	NPC277351
0.7703	Intermediate Similarity	NPC51388
0.7696	Intermediate Similarity	NPC475844
0.7696	Intermediate Similarity	NPC476287
0.7692	Intermediate Similarity	NPC26543
0.7692	Intermediate Similarity	NPC70259
0.7688	Intermediate Similarity	NPC56618
0.7681	Intermediate Similarity	NPC473178
0.7678	Intermediate Similarity	NPC267423
0.7674	Intermediate Similarity	NPC201697
0.7671	Intermediate Similarity	NPC314552
0.7667	Intermediate Similarity	NPC476167
0.7655	Intermediate Similarity	NPC476451
0.7653	Intermediate Similarity	NPC475070
0.7647	Intermediate Similarity	NPC86078
0.7644	Intermediate Similarity	NPC205934
0.7644	Intermediate Similarity	NPC43787
0.7644	Intermediate Similarity	NPC253580
0.7642	Intermediate Similarity	NPC135887
0.7642	Intermediate Similarity	NPC199277
0.7639	Intermediate Similarity	NPC11464
0.7636	Intermediate Similarity	NPC303658
0.7635	Intermediate Similarity	NPC84478
0.7633	Intermediate Similarity	NPC99666
0.7619	Intermediate Similarity	NPC192315
0.7617	Intermediate Similarity	NPC45190
0.7604	Intermediate Similarity	NPC294375
0.76	Intermediate Similarity	NPC470126
0.7598	Intermediate Similarity	NPC42591
0.7598	Intermediate Similarity	NPC94943
0.7598	Intermediate Similarity	NPC295228
0.7597	Intermediate Similarity	NPC208522
0.7593	Intermediate Similarity	NPC476116
0.7591	Intermediate Similarity	NPC304926
0.7591	Intermediate Similarity	NPC476041
0.7581	Intermediate Similarity	NPC283117
0.7577	Intermediate Similarity	NPC474701
0.7573	Intermediate Similarity	NPC128751
0.7571	Intermediate Similarity	NPC153042
0.7569	Intermediate Similarity	NPC294620
0.7565	Intermediate Similarity	NPC15801
0.7563	Intermediate Similarity	NPC478080
0.7561	Intermediate Similarity	NPC171171
0.7558	Intermediate Similarity	NPC167860
0.7558	Intermediate Similarity	NPC123976
0.7557	Intermediate Similarity	NPC96321
0.7549	Intermediate Similarity	NPC190007
0.7546	Intermediate Similarity	NPC470931
0.7544	Intermediate Similarity	NPC474192
0.7544	Intermediate Similarity	NPC475720
0.7543	Intermediate Similarity	NPC477066
0.7536	Intermediate Similarity	NPC469497
0.7536	Intermediate Similarity	NPC106833
0.7535	Intermediate Similarity	NPC477113
0.7535	Intermediate Similarity	NPC300156
0.7534	Intermediate Similarity	NPC310118
0.7522	Intermediate Similarity	NPC110151
0.7512	Intermediate Similarity	NPC314002
0.7512	Intermediate Similarity	NPC476044
0.7511	Intermediate Similarity	NPC313884
0.7511	Intermediate Similarity	NPC329631
0.7511	Intermediate Similarity	NPC293151
0.7511	Intermediate Similarity	NPC478081
0.7511	Intermediate Similarity	NPC98371
0.75	Intermediate Similarity	NPC212535
0.75	Intermediate Similarity	NPC477861
0.7489	Intermediate Similarity	NPC316981
0.7488	Intermediate Similarity	NPC274291
0.7488	Intermediate Similarity	NPC264166
0.7488	Intermediate Similarity	NPC77555
0.7488	Intermediate Similarity	NPC329708
0.7488	Intermediate Similarity	NPC118832
0.7488	Intermediate Similarity	NPC47059
0.7488	Intermediate Similarity	NPC470500
0.7488	Intermediate Similarity	NPC165349
0.7478	Intermediate Similarity	NPC103687
0.7478	Intermediate Similarity	NPC132631
0.7463	Intermediate Similarity	NPC204717
0.7462	Intermediate Similarity	NPC118511
0.7458	Intermediate Similarity	NPC53534
0.7457	Intermediate Similarity	NPC470784
0.7445	Intermediate Similarity	NPC6215
0.7444	Intermediate Similarity	NPC292958
0.7443	Intermediate Similarity	NPC87413
0.7438	Intermediate Similarity	NPC89549
0.7436	Intermediate Similarity	NPC478082
0.7436	Intermediate Similarity	NPC477067
0.743	Intermediate Similarity	NPC232727
0.7426	Intermediate Similarity	NPC134586
0.7418	Intermediate Similarity	NPC152620
0.7415	Intermediate Similarity	NPC220765
0.7414	Intermediate Similarity	NPC184680
0.7413	Intermediate Similarity	NPC34508
0.7412	Intermediate Similarity	NPC476997
0.7411	Intermediate Similarity	NPC150239
0.7393	Intermediate Similarity	NPC195314
0.7391	Intermediate Similarity	NPC49547
0.7389	Intermediate Similarity	NPC211997
0.7387	Intermediate Similarity	NPC469928
0.7385	Intermediate Similarity	NPC314957
0.7382	Intermediate Similarity	NPC470785

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 NPC132642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	659
0.2-0.3	904
0.3-0.4	1417
0.4-0.5	2710
0.5-0.6	2189
0.6-0.7	826
0.7-0.8	173
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.835	Intermediate Similarity	NPD7222	Phase 2
0.8261	Intermediate Similarity	NPD7453	Approved
0.8261	Intermediate Similarity	NPD7452	Approved
0.8098	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD4502	Phase 2
0.7991	Intermediate Similarity	NPD5902	Approved
0.7991	Intermediate Similarity	NPD5903	Approved
0.7982	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3003	Approved
0.7941	Intermediate Similarity	NPD1038	Approved
0.7926	Intermediate Similarity	NPD3875	Discontinued
0.7888	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5612	Discontinued
0.7861	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6985	Discontinued
0.7793	Intermediate Similarity	NPD5658	Approved
0.7767	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7194	Discontinued
0.7756	Intermediate Similarity	NPD5913	Phase 3
0.7756	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7743	Intermediate Similarity	NPD7558	Phase 2
0.77	Intermediate Similarity	NPD5530	Phase 1
0.7685	Intermediate Similarity	NPD5936	Approved
0.7685	Intermediate Similarity	NPD5939	Approved
0.7681	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD5164	Discontinued
0.7667	Intermediate Similarity	NPD8395	Approved
0.7667	Intermediate Similarity	NPD8396	Approved
0.7667	Intermediate Similarity	NPD1768	Approved
0.7617	Intermediate Similarity	NPD8403	Phase 1
0.7583	Intermediate Similarity	NPD3825	Phase 3
0.7583	Intermediate Similarity	NPD2177	Approved
0.7583	Intermediate Similarity	NPD2175	Phase 3
0.7583	Intermediate Similarity	NPD2176	Approved
0.7571	Intermediate Similarity	NPD7948	Phase 1
0.7566	Intermediate Similarity	NPD5559	Phase 2
0.7566	Intermediate Similarity	NPD7555	Discontinued
0.7561	Intermediate Similarity	NPD5256	Discontinued
0.756	Intermediate Similarity	NPD4418	Discontinued
0.7557	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD4203	Approved
0.7537	Intermediate Similarity	NPD4204	Approved
0.7523	Intermediate Similarity	NPD3402	Phase 1
0.7523	Intermediate Similarity	NPD5067	Phase 2
0.7523	Intermediate Similarity	NPD5066	Phase 2
0.7522	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD4454	Phase 2
0.7522	Intermediate Similarity	NPD6978	Phase 2
0.7512	Intermediate Similarity	NPD4511	Phase 1
0.7511	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD6494	Phase 2
0.7511	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.751	Intermediate Similarity	NPD8364	Approved
0.751	Intermediate Similarity	NPD8363	Approved
0.75	Intermediate Similarity	NPD6290	Phase 2
0.75	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1392	Approved
0.7489	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD4039	Approved
0.7488	Intermediate Similarity	NPD4033	Approved
0.7488	Intermediate Similarity	NPD4035	Approved
0.7488	Intermediate Similarity	NPD4122	Approved
0.7488	Intermediate Similarity	NPD4037	Approved
0.7488	Intermediate Similarity	NPD4038	Approved
0.7488	Intermediate Similarity	NPD32	Approved
0.7488	Intermediate Similarity	NPD4034	Approved
0.7488	Intermediate Similarity	NPD31	Approved
0.7488	Intermediate Similarity	NPD4036	Approved
0.7487	Intermediate Similarity	NPD1326	Approved
0.7487	Intermediate Similarity	NPD1325	Approved
0.7475	Intermediate Similarity	NPD6159	Phase 2
0.7465	Intermediate Similarity	NPD7671	Approved
0.7465	Intermediate Similarity	NPD7672	Approved
0.7449	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6456	Discontinued
0.7411	Intermediate Similarity	NPD6242	Discontinued
0.7409	Intermediate Similarity	NPD3330	Phase 1
0.7401	Intermediate Similarity	NPD7603	Discontinued
0.7393	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8244	Phase 2
0.7373	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6220	Phase 3
0.7361	Intermediate Similarity	NPD6991	Approved
0.7358	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7221	Approved
0.7345	Intermediate Similarity	NPD7219	Approved
0.7343	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5429	Discontinued
0.7333	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5003	Discontinued
0.7321	Intermediate Similarity	NPD7395	Discontinued
0.7316	Intermediate Similarity	NPD4885	Approved
0.7311	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8358	Approved
0.7306	Intermediate Similarity	NPD2189	Approved
0.7306	Intermediate Similarity	NPD2187	Approved
0.7304	Intermediate Similarity	NPD5479	Discontinued
0.7304	Intermediate Similarity	NPD7567	Approved
0.7301	Intermediate Similarity	NPD7726	Phase 1
0.7299	Intermediate Similarity	NPD6569	Phase 2
0.7296	Intermediate Similarity	NPD3006	Discontinued
0.7289	Intermediate Similarity	NPD6455	Phase 3
0.7273	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7659	Discontinued
0.7257	Intermediate Similarity	NPD7068	Approved
0.7257	Intermediate Similarity	NPD7067	Approved
0.7256	Intermediate Similarity	NPD5999	Phase 2
0.7246	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5632	Approved
0.7244	Intermediate Similarity	NPD4429	Discontinued
0.7241	Intermediate Similarity	NPD3746	Discontinued
0.7241	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6595	Phase 3
0.7232	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6643	Discontinued
0.723	Intermediate Similarity	NPD6590	Discontinued
0.7229	Intermediate Similarity	NPD5022	Discontinued
0.722	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6517	Phase 3
0.7212	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5416	Discontinued
0.7203	Intermediate Similarity	NPD8016	Phase 3
0.7203	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3477	Phase 2
0.7195	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD8466	Approved
0.7194	Intermediate Similarity	NPD8429	Approved
0.7194	Intermediate Similarity	NPD8467	Approved
0.7194	Intermediate Similarity	NPD8428	Approved
0.7194	Intermediate Similarity	NPD8465	Approved
0.7194	Intermediate Similarity	NPD8427	Approved
0.7193	Intermediate Similarity	NPD6995	Phase 1
0.719	Intermediate Similarity	NPD2383	Phase 1
0.7188	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5021	Discontinued
0.7177	Intermediate Similarity	NPD3343	Phase 3
0.7172	Intermediate Similarity	NPD6961	Discontinued
0.7169	Intermediate Similarity	NPD4795	Phase 2
0.7168	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5596	Phase 2
0.7156	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5044	Phase 2
0.7149	Intermediate Similarity	NPD4442	Phase 2
0.7149	Intermediate Similarity	NPD7853	Phase 2
0.7143	Intermediate Similarity	NPD7994	Phase 2
0.7143	Intermediate Similarity	NPD6473	Phase 1
0.7143	Intermediate Similarity	NPD6716	Phase 1
0.7143	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD3763	Approved
0.7136	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD8442	Discontinued
0.713	Intermediate Similarity	NPD7470	Discontinued
0.7123	Intermediate Similarity	NPD2564	Approved
0.7123	Intermediate Similarity	NPD2565	Phase 2
0.7119	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4343	Phase 1
0.7118	Intermediate Similarity	NPD6736	Discontinued
0.7118	Intermediate Similarity	NPD1856	Discontinued
0.7116	Intermediate Similarity	NPD5512	Phase 3
0.7107	Intermediate Similarity	NPD6243	Phase 3
0.7107	Intermediate Similarity	NPD8101	Phase 3
0.7107	Intermediate Similarity	NPD5482	Discontinued
0.7107	Intermediate Similarity	NPD6244	Phase 3
0.7101	Intermediate Similarity	NPD7417	Discontinued
0.7101	Intermediate Similarity	NPD3920	Phase 2
0.7089	Intermediate Similarity	NPD6750	Phase 2
0.7085	Intermediate Similarity	NPD6531	Approved
0.7085	Intermediate Similarity	NPD6530	Approved
0.7083	Intermediate Similarity	NPD6988	Phase 1
0.7082	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD8426	Approved
0.7082	Intermediate Similarity	NPD8460	Approved
0.7082	Intermediate Similarity	NPD8425	Approved
0.7082	Intermediate Similarity	NPD8459	Approved
0.708	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6452	Discontinued
0.7064	Intermediate Similarity	NPD484	Approved
0.7064	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4890	Phase 2
0.7056	Intermediate Similarity	NPD3923	Approved
0.7056	Intermediate Similarity	NPD3922	Approved
0.7056	Intermediate Similarity	NPD3921	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