NPASS Compound

Structure

NPC246700 OpenBabel07101718322D 25 27 0 0 0 0 0 0 0 0999 V2000 1.7187 8.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3175 9.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3566 4.9586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5431 6.7857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1364 7.6993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0446 5.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2257 4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 3.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7242 8.5083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3621 5.0632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 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 -1.8080 3.5497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	333.21
Volume:	379.39
LogP:	6.786
LogD:	4.866
LogS:	-4.383
# Rotatable Bonds:	5
TPSA:	36.02
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	2.664
Fsp3:	0.304
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:	-5.023
MDCK Permeability:	1.4810977518209256e-05
Pgp-inhibitor:	0.947
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	99.60955047607422%
Volume Distribution (VD):	1.769
Pgp-substrate:	1.335532546043396%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.366
CYP2C19-inhibitor:	0.908
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.925
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	5.872
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.957
Carcinogencity:	0.126
Eye Corrosion:	0.03
Eye Irritation:	0.966
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC246700

Natural Product ID:	NPC246700
*Common Name:**	Eustifoline C
IUPAC Name:	4-[(2E)-3,7-dimethylocta-2,6-dienyl]-6-methyl-9H-carbazol-3-ol
Synonyms:	Eustifoline C
Standard InCHIKey:	MFGOZKCFDYMVEK-LZYBPNLTSA-N
Standard InCHI:	InChI=1S/C23H27NO/c1-15(2)6-5-7-16(3)8-10-18-22(25)13-12-21-23(18)19-14-17(4)9-11-20(19)24-21/h6,8-9,11-14,24-25H,5,7,10H2,1-4H3/b16-8+
SMILES:	C/C(=CCc1c(O)ccc2c1c1cc(C)ccc1[nH]2)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2323765
PubChem CID:	14635307
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
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662104]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[23376010]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	fruits	Coimbatore, India	2010-JUN	PMID[23691929]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27136692]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	12

Activity Type	# Activity
Individual Protein	5
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	16.1	%	PMID[518790]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	5.9	%	PMID[518790]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	2.3	%	PMID[518790]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	2.7	%	PMID[518790]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	1.0	%	PMID[518790]
NPT27	Others	Unspecified		Activity	=	9.9	%	PMID[518790]
NPT27	Others	Unspecified		Activity	=	79.2	%	PMID[518790]
NPT27	Others	Unspecified		Activity	=	96.5	%	PMID[518790]
NPT27	Others	Unspecified		Activity	=	104.5	%	PMID[518790]
NPT2	Others	Unspecified		IC50	=	8300.0	nM	PMID[518790]
NPT2	Others	Unspecified		Inhibition	=	55.9	%	PMID[518790]
NPT2	Others	Unspecified		Inhibition	=	25.2	%	PMID[518790]
NPT2	Others	Unspecified		Inhibition	=	19.7	%	PMID[518790]

☑ 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 NPC246700 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	562
0.1-0.2	3614
0.2-0.3	13577
0.3-0.4	8935
0.4-0.5	10849
0.5-0.6	3090
0.6-0.7	1623
0.7-0.8	377
0.8-0.85	49
0.85-0.9	10
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9763	High Similarity	NPC128751
0.9706	High Similarity	NPC469497
0.9706	High Similarity	NPC106833
0.9598	High Similarity	NPC153042
0.9521	High Similarity	NPC88363
0.9133	High Similarity	NPC94943
0.9126	High Similarity	NPC193777
0.9075	High Similarity	NPC190007
0.9017	High Similarity	NPC212535
0.893	High Similarity	NPC9894
0.8883	High Similarity	NPC48353
0.883	High Similarity	NPC474409
0.8634	High Similarity	NPC70956
0.8634	High Similarity	NPC243834
0.8526	High Similarity	NPC201697
0.8525	High Similarity	NPC131017
0.8516	High Similarity	NPC99666
0.8444	Intermediate Similarity	NPC171171
0.8436	Intermediate Similarity	NPC204717
0.8404	Intermediate Similarity	NPC291535
0.8404	Intermediate Similarity	NPC475085
0.8404	Intermediate Similarity	NPC475112
0.8389	Intermediate Similarity	NPC314002
0.838	Intermediate Similarity	NPC220765
0.836	Intermediate Similarity	NPC162484
0.8315	Intermediate Similarity	NPC72980
0.8267	Intermediate Similarity	NPC252251
0.8263	Intermediate Similarity	NPC223427
0.8258	Intermediate Similarity	NPC184964
0.8247	Intermediate Similarity	NPC208284
0.8245	Intermediate Similarity	NPC128823
0.8235	Intermediate Similarity	NPC77555
0.8227	Intermediate Similarity	NPC209174
0.822	Intermediate Similarity	NPC475070
0.8201	Intermediate Similarity	NPC249040
0.8186	Intermediate Similarity	NPC477531
0.8182	Intermediate Similarity	NPC70259
0.8177	Intermediate Similarity	NPC176127
0.8152	Intermediate Similarity	NPC242928
0.8131	Intermediate Similarity	NPC293151
0.8131	Intermediate Similarity	NPC314552
0.8128	Intermediate Similarity	NPC276517
0.8128	Intermediate Similarity	NPC43787
0.8128	Intermediate Similarity	NPC205934
0.8115	Intermediate Similarity	NPC135887
0.8115	Intermediate Similarity	NPC199277
0.8112	Intermediate Similarity	NPC294620
0.8095	Intermediate Similarity	NPC72211
0.809	Intermediate Similarity	NPC477609
0.8087	Intermediate Similarity	NPC476319
0.8083	Intermediate Similarity	NPC476106
0.8071	Intermediate Similarity	NPC478074
0.8063	Intermediate Similarity	NPC267423
0.8061	Intermediate Similarity	NPC294375
0.8061	Intermediate Similarity	NPC23294
0.806	Intermediate Similarity	NPC280799
0.8051	Intermediate Similarity	NPC476116
0.802	Intermediate Similarity	NPC473180
0.801	Intermediate Similarity	NPC303951
0.798	Intermediate Similarity	NPC51388
0.7978	Intermediate Similarity	NPC280548
0.796	Intermediate Similarity	NPC473179
0.7959	Intermediate Similarity	NPC473181
0.7959	Intermediate Similarity	NPC209769
0.7951	Intermediate Similarity	NPC470126
0.7947	Intermediate Similarity	NPC156704
0.7937	Intermediate Similarity	NPC195314
0.7921	Intermediate Similarity	NPC86078
0.7919	Intermediate Similarity	NPC199667
0.7919	Intermediate Similarity	NPC5145
0.7917	Intermediate Similarity	NPC329793
0.7913	Intermediate Similarity	NPC253580
0.7908	Intermediate Similarity	NPC86834
0.7908	Intermediate Similarity	NPC210828
0.7905	Intermediate Similarity	NPC6786
0.7903	Intermediate Similarity	NPC46580
0.79	Intermediate Similarity	NPC469928
0.7897	Intermediate Similarity	NPC300156
0.7897	Intermediate Similarity	NPC45190
0.7895	Intermediate Similarity	NPC251090
0.7887	Intermediate Similarity	NPC476098
0.7884	Intermediate Similarity	NPC307963
0.7876	Intermediate Similarity	NPC476044
0.7869	Intermediate Similarity	NPC478032
0.7857	Intermediate Similarity	NPC283117
0.7853	Intermediate Similarity	NPC159319
0.7847	Intermediate Similarity	NPC473182
0.7826	Intermediate Similarity	NPC477608
0.7826	Intermediate Similarity	NPC474798
0.7824	Intermediate Similarity	NPC213308
0.7819	Intermediate Similarity	NPC76748
0.7817	Intermediate Similarity	NPC39679
0.7801	Intermediate Similarity	NPC242209
0.78	Intermediate Similarity	NPC477610
0.78	Intermediate Similarity	NPC266931
0.7797	Intermediate Similarity	NPC16667
0.7794	Intermediate Similarity	NPC477532
0.779	Intermediate Similarity	NPC34508
0.779	Intermediate Similarity	NPC259545
0.7784	Intermediate Similarity	NPC19679
0.7778	Intermediate Similarity	NPC473185
0.7778	Intermediate Similarity	NPC92111
0.7772	Intermediate Similarity	NPC476041
0.7772	Intermediate Similarity	NPC304926
0.7771	Intermediate Similarity	NPC141353
0.7771	Intermediate Similarity	NPC184476
0.7766	Intermediate Similarity	NPC296527
0.7766	Intermediate Similarity	NPC32771
0.7761	Intermediate Similarity	NPC118228
0.776	Intermediate Similarity	NPC474188
0.7756	Intermediate Similarity	NPC280272
0.7753	Intermediate Similarity	NPC32028
0.7749	Intermediate Similarity	NPC326634
0.7745	Intermediate Similarity	NPC150239
0.7745	Intermediate Similarity	NPC132642
0.7732	Intermediate Similarity	NPC315491
0.7732	Intermediate Similarity	NPC45459
0.7729	Intermediate Similarity	NPC227908
0.7729	Intermediate Similarity	NPC202503
0.7727	Intermediate Similarity	NPC470931
0.7727	Intermediate Similarity	NPC477111
0.7723	Intermediate Similarity	NPC183407
0.7723	Intermediate Similarity	NPC3207
0.7722	Intermediate Similarity	NPC154293
0.7718	Intermediate Similarity	NPC211416
0.7708	Intermediate Similarity	NPC205403
0.7704	Intermediate Similarity	NPC477135
0.7697	Intermediate Similarity	NPC47298
0.7697	Intermediate Similarity	NPC315214
0.7692	Intermediate Similarity	NPC471294
0.768	Intermediate Similarity	NPC476167
0.7677	Intermediate Similarity	NPC270918
0.7667	Intermediate Similarity	NPC474701
0.7665	Intermediate Similarity	NPC470930
0.7663	Intermediate Similarity	NPC96890
0.7662	Intermediate Similarity	NPC94157
0.7656	Intermediate Similarity	NPC274640
0.7656	Intermediate Similarity	NPC477607
0.765	Intermediate Similarity	NPC471304
0.765	Intermediate Similarity	NPC11464
0.7647	Intermediate Similarity	NPC46561
0.7647	Intermediate Similarity	NPC84478
0.7647	Intermediate Similarity	NPC60553
0.7647	Intermediate Similarity	NPC247803
0.7644	Intermediate Similarity	NPC324149
0.7641	Intermediate Similarity	NPC176538
0.7629	Intermediate Similarity	NPC306376
0.7629	Intermediate Similarity	NPC192315
0.7626	Intermediate Similarity	NPC477113
0.7622	Intermediate Similarity	NPC232340
0.7622	Intermediate Similarity	NPC270009
0.7622	Intermediate Similarity	NPC472443
0.7617	Intermediate Similarity	NPC222018
0.7612	Intermediate Similarity	NPC87413
0.7606	Intermediate Similarity	NPC473189
0.7604	Intermediate Similarity	NPC106937
0.759	Intermediate Similarity	NPC476175
0.759	Intermediate Similarity	NPC32200
0.7588	Intermediate Similarity	NPC88008
0.7586	Intermediate Similarity	NPC124005
0.7585	Intermediate Similarity	NPC144452
0.7584	Intermediate Similarity	NPC67056
0.7582	Intermediate Similarity	NPC126481
0.7573	Intermediate Similarity	NPC225279
0.7571	Intermediate Similarity	NPC285469
0.7561	Intermediate Similarity	NPC184408
0.7552	Intermediate Similarity	NPC280964
0.7552	Intermediate Similarity	NPC141915
0.7552	Intermediate Similarity	NPC114335
0.7551	Intermediate Similarity	NPC329747
0.754	Intermediate Similarity	NPC314394
0.754	Intermediate Similarity	NPC192270
0.7539	Intermediate Similarity	NPC95783
0.7524	Intermediate Similarity	NPC6215
0.7514	Intermediate Similarity	NPC38736
0.7514	Intermediate Similarity	NPC207726
0.7513	Intermediate Similarity	NPC475190
0.75	Intermediate Similarity	NPC472444
0.75	Intermediate Similarity	NPC313791
0.7488	Intermediate Similarity	NPC473183
0.7488	Intermediate Similarity	NPC316981
0.7488	Intermediate Similarity	NPC174760
0.7487	Intermediate Similarity	NPC198339
0.7465	Intermediate Similarity	NPC132329
0.7463	Intermediate Similarity	NPC475910
0.7463	Intermediate Similarity	NPC477110
0.7463	Intermediate Similarity	NPC330009
0.7462	Intermediate Similarity	NPC11017
0.7459	Intermediate Similarity	NPC472587
0.7444	Intermediate Similarity	NPC131718
0.7444	Intermediate Similarity	NPC473320
0.7443	Intermediate Similarity	NPC160898
0.7436	Intermediate Similarity	NPC472193
0.7432	Intermediate Similarity	NPC44161
0.7429	Intermediate Similarity	NPC179287
0.7425	Intermediate Similarity	NPC475450
0.7425	Intermediate Similarity	NPC179365
0.7419	Intermediate Similarity	NPC288785
0.7418	Intermediate Similarity	NPC470508
0.7416	Intermediate Similarity	NPC162748

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 NPC246700 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	703
0.2-0.3	850
0.3-0.4	1425
0.4-0.5	2913
0.5-0.6	2129
0.6-0.7	681
0.7-0.8	101
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8548	High Similarity	NPD4511	Phase 1
0.847	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD1326	Approved
0.8391	Intermediate Similarity	NPD1325	Approved
0.8287	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD5164	Discontinued
0.8053	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD1038	Approved
0.788	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD8396	Approved
0.7865	Intermediate Similarity	NPD8395	Approved
0.7853	Intermediate Similarity	NPD7948	Phase 1
0.7842	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5936	Approved
0.7789	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5939	Approved
0.7772	Intermediate Similarity	NPD2177	Approved
0.7772	Intermediate Similarity	NPD2176	Approved
0.7772	Intermediate Similarity	NPD2175	Phase 3
0.7732	Intermediate Similarity	NPD484	Approved
0.7697	Intermediate Similarity	NPD1684	Approved
0.7697	Intermediate Similarity	NPD1685	Approved
0.7678	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD5658	Approved
0.7638	Intermediate Similarity	NPD2916	Discontinued
0.7635	Intermediate Similarity	NPD5612	Discontinued
0.7635	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD3003	Approved
0.7626	Intermediate Similarity	NPD5530	Phase 1
0.7604	Intermediate Similarity	NPD802	Phase 2
0.759	Intermediate Similarity	NPD3814	Phase 1
0.7576	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6975	Discontinued
0.7544	Intermediate Similarity	NPD1592	Phase 3
0.7538	Intermediate Similarity	NPD2727	Phase 2
0.7526	Intermediate Similarity	NPD2383	Phase 1
0.75	Intermediate Similarity	NPD7453	Approved
0.75	Intermediate Similarity	NPD7222	Phase 2
0.75	Intermediate Similarity	NPD7452	Approved
0.75	Intermediate Similarity	NPD6290	Phase 2
0.7488	Intermediate Similarity	NPD2794	Discontinued
0.7474	Intermediate Similarity	NPD4418	Discontinued
0.7473	Intermediate Similarity	NPD6159	Phase 2
0.7459	Intermediate Similarity	NPD5065	Approved
0.7438	Intermediate Similarity	NPD4502	Phase 2
0.7409	Intermediate Similarity	NPD5913	Phase 3
0.7409	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD6158	Phase 2
0.7401	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD3928	Approved
0.7387	Intermediate Similarity	NPD3931	Approved
0.7356	Intermediate Similarity	NPD5254	Discontinued
0.7345	Intermediate Similarity	NPD4462	Approved
0.7345	Intermediate Similarity	NPD4463	Approved
0.734	Intermediate Similarity	NPD8386	Phase 2
0.734	Intermediate Similarity	NPD3920	Phase 2
0.7337	Intermediate Similarity	NPD2844	Phase 3
0.733	Intermediate Similarity	NPD5902	Approved
0.733	Intermediate Similarity	NPD5903	Approved
0.733	Intermediate Similarity	NPD2762	Phase 2
0.7323	Intermediate Similarity	NPD3825	Phase 3
0.7323	Intermediate Similarity	NPD1768	Approved
0.7322	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5003	Discontinued
0.7303	Intermediate Similarity	NPD2882	Phase 1
0.7302	Intermediate Similarity	NPD3746	Discontinued
0.7296	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7112	Discontinued
0.7291	Intermediate Similarity	NPD2189	Approved
0.7291	Intermediate Similarity	NPD2187	Approved
0.7278	Intermediate Similarity	NPD2789	Approved
0.7277	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5140	Approved
0.7268	Intermediate Similarity	NPD5138	Approved
0.7254	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5599	Discontinued
0.7251	Intermediate Similarity	NPD7221	Approved
0.7251	Intermediate Similarity	NPD7219	Approved
0.7243	Intermediate Similarity	NPD1921	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3330	Phase 1
0.7228	Intermediate Similarity	NPD4795	Phase 2
0.7228	Intermediate Similarity	NPD5901	Discontinued
0.7225	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2021	Discontinued
0.7225	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6376	Discontinued
0.72	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3404	Approved
0.7179	Intermediate Similarity	NPD2565	Phase 2
0.7179	Intermediate Similarity	NPD2564	Approved
0.7172	Intermediate Similarity	NPD3127	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8431	Approved
0.7158	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6242	Discontinued
0.7151	Intermediate Similarity	NPD5021	Discontinued
0.7143	Intermediate Similarity	NPD2380	Approved
0.7143	Intermediate Similarity	NPD2381	Approved
0.7143	Intermediate Similarity	NPD2382	Approved
0.7136	Intermediate Similarity	NPD1219	Approved
0.7136	Intermediate Similarity	NPD1218	Approved
0.7123	Intermediate Similarity	NPD5507	Approved
0.7123	Intermediate Similarity	NPD5506	Approved
0.7115	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1739	Approved
0.7114	Intermediate Similarity	NPD1740	Approved
0.7105	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5067	Phase 2
0.7101	Intermediate Similarity	NPD5066	Phase 2
0.7094	Intermediate Similarity	NPD2920	Discontinued
0.7086	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4203	Approved
0.7083	Intermediate Similarity	NPD4204	Approved
0.7079	Intermediate Similarity	NPD6145	Phase 1
0.7075	Intermediate Similarity	NPD5930	Phase 3
0.7073	Intermediate Similarity	NPD1392	Approved
0.7068	Intermediate Similarity	NPD4079	Approved
0.7068	Intermediate Similarity	NPD4076	Approved
0.7062	Intermediate Similarity	NPD6985	Discontinued
0.7053	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7726	Phase 1
0.7037	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6595	Phase 3
0.7028	Intermediate Similarity	NPD7194	Discontinued
0.7021	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6220	Phase 3
0.7016	Intermediate Similarity	NPD3506	Approved
0.7016	Intermediate Similarity	NPD3505	Approved
0.7011	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4044	Discontinued
0.7005	Intermediate Similarity	NPD7555	Discontinued
0.7005	Intermediate Similarity	NPD5559	Phase 2
0.7	Intermediate Similarity	NPD6492	Phase 2
0.6991	Remote Similarity	NPD7603	Discontinued
0.6991	Remote Similarity	NPD8358	Approved
0.6986	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5100	Phase 3
0.6961	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5596	Phase 2
0.6955	Remote Similarity	NPD6494	Phase 2
0.6955	Remote Similarity	NPD7558	Phase 2
0.6954	Remote Similarity	NPD1534	Approved
0.695	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3258	Approved
0.6948	Remote Similarity	NPD3875	Discontinued
0.6947	Remote Similarity	NPD7418	Discontinued
0.6946	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3921	Approved
0.6935	Remote Similarity	NPD3924	Approved
0.6935	Remote Similarity	NPD3922	Approved
0.6935	Remote Similarity	NPD3923	Approved
0.6934	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5810	Discontinued
0.6914	Remote Similarity	NPD1262	Discovery
0.6911	Remote Similarity	NPD7324	Discontinued
0.6911	Remote Similarity	NPD9690	Approved
0.6908	Remote Similarity	NPD5429	Discontinued
0.6907	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4948	Discontinued
0.6901	Remote Similarity	NPD5632	Approved
0.6901	Remote Similarity	NPD3354	Phase 2
0.6895	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD112	Approved
0.6882	Remote Similarity	NPD9705	Discontinued
0.6881	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4845	Discontinued
0.6881	Remote Similarity	NPD6978	Phase 2
0.6881	Remote Similarity	NPD2952	Discontinued
0.6875	Remote Similarity	NPD7671	Approved
0.6875	Remote Similarity	NPD7672	Approved
0.6872	Remote Similarity	NPD2615	Phase 3
0.6872	Remote Similarity	NPD2616	Phase 3
0.6872	Remote Similarity	NPD5488	Discontinued
0.6869	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3835	Phase 3
0.6868	Remote Similarity	NPD3833	Phase 3
0.6863	Remote Similarity	NPD4601	Approved
0.6863	Remote Similarity	NPD4600	Approved
0.686	Remote Similarity	NPD8403	Phase 1
0.686	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6452	Discontinued
0.6852	Remote Similarity	NPD6736	Discontinued
0.6845	Remote Similarity	NPD4886	Phase 2
0.6842	Remote Similarity	NPD7474	Suspended
0.684	Remote Similarity	NPD4897	Phase 2
0.6839	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2144	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