NPASS Compound

Structure

NPC284141 OpenBabel07101719252D 35 39 0 0 0 0 0 0 0 0999 V2000 -1.0803 5.0826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9052 3.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7202 3.3884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 2.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0540 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3675 3.9236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3894 4.1315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2653 1.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 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 0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 -0.2738 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6666 2.1759 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0366 4.6668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 18 2 0 0 0 0 9 19 2 0 0 0 0 10 23 2 0 0 0 0 11 24 2 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 30 1 0 0 0 0 15 22 2 0 0 0 0 15 31 1 0 0 0 0 16 17 1 0 0 0 0 16 32 1 0 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 20 28 2 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 29 2 0 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.2
Volume:	492.875
LogP:	5.226
LogD:	3.548
LogS:	-3.337
# Rotatable Bonds:	7
TPSA:	90.5
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	3.022
Fsp3:	0.172
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.293
MDCK Permeability:	7.539999387518037e-06
Pgp-inhibitor:	0.251
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	99.24329376220703%
Volume Distribution (VD):	0.32
Pgp-substrate:	1.1110013723373413%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.567
CYP2C19-inhibitor:	0.972
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.916
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.824
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	3.892
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.246
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.257
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.413
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.627

Download Data

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

Natural Product: NPC284141

Natural Product ID:	NPC284141
*Common Name:**	Ochrindole B
IUPAC Name:	4-[(E)-4-hydroxy-3-methylbut-2-enyl]-2,5-bis(1H-indol-3-yl)-3,6-dimethoxyphenol
Synonyms:
Standard InCHIKey:	WFEYRYIESDXIIL-SFQUDFHCSA-N
Standard InCHI:	InChI=1S/C29H28N2O4/c1-17(16-32)12-13-20-25(21-14-30-23-10-6-4-8-18(21)23)29(35-3)27(33)26(28(20)34-2)22-15-31-24-11-7-5-9-19(22)24/h4-12,14-15,30-33H,13,16H2,1-3H3/b17-12+
SMILES:	C/C(=CCc1c(c2c[nH]c3ccccc23)c(c(c(c2c[nH]c3ccccc23)c1OC)O)OC)/CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517999
PubChem CID:	11754391
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002334] Phenylpyrroles

*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
NPO33431	aspergillus ochraceus nrrl 3519	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064296]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	15.0	mm	PMID[455172]

☑ 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 NPC284141 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	598
0.1-0.2	3151
0.2-0.3	12880
0.3-0.4	5428
0.4-0.5	12158
0.5-0.6	6121
0.6-0.7	2008
0.7-0.8	329
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC217554
0.9767	High Similarity	NPC11408
0.8532	High Similarity	NPC266931
0.8475	Intermediate Similarity	NPC122463
0.8386	Intermediate Similarity	NPC174049
0.8225	Intermediate Similarity	NPC255800
0.8225	Intermediate Similarity	NPC96584
0.8153	Intermediate Similarity	NPC316981
0.8133	Intermediate Similarity	NPC473822
0.813	Intermediate Similarity	NPC476997
0.812	Intermediate Similarity	NPC473183
0.8112	Intermediate Similarity	NPC473184
0.8095	Intermediate Similarity	NPC476998
0.8095	Intermediate Similarity	NPC476996
0.807	Intermediate Similarity	NPC118121
0.806	Intermediate Similarity	NPC201508
0.8053	Intermediate Similarity	NPC204446
0.8052	Intermediate Similarity	NPC476994
0.8	Intermediate Similarity	NPC295228
0.7991	Intermediate Similarity	NPC473182
0.7965	Intermediate Similarity	NPC170114
0.7957	Intermediate Similarity	NPC277351
0.7946	Intermediate Similarity	NPC208284
0.792	Intermediate Similarity	NPC470549
0.7911	Intermediate Similarity	NPC202605
0.7911	Intermediate Similarity	NPC112206
0.7826	Intermediate Similarity	NPC132642
0.7823	Intermediate Similarity	NPC89549
0.7822	Intermediate Similarity	NPC11464
0.7815	Intermediate Similarity	NPC476995
0.7801	Intermediate Similarity	NPC15406
0.7798	Intermediate Similarity	NPC251090
0.7783	Intermediate Similarity	NPC46451
0.7778	Intermediate Similarity	NPC473185
0.7778	Intermediate Similarity	NPC110151
0.7763	Intermediate Similarity	NPC235076
0.7759	Intermediate Similarity	NPC280272
0.7748	Intermediate Similarity	NPC135887
0.7748	Intermediate Similarity	NPC199277
0.7745	Intermediate Similarity	NPC252251
0.7743	Intermediate Similarity	NPC188420
0.7739	Intermediate Similarity	NPC100079
0.7739	Intermediate Similarity	NPC23614
0.7719	Intermediate Similarity	NPC149471
0.7719	Intermediate Similarity	NPC271215
0.7706	Intermediate Similarity	NPC307963
0.7683	Intermediate Similarity	NPC183537
0.7683	Intermediate Similarity	NPC77878
0.7682	Intermediate Similarity	NPC224928
0.7679	Intermediate Similarity	NPC164374
0.7679	Intermediate Similarity	NPC137929
0.7679	Intermediate Similarity	NPC477531
0.7675	Intermediate Similarity	NPC251160
0.7661	Intermediate Similarity	NPC133140
0.7661	Intermediate Similarity	NPC195268
0.7661	Intermediate Similarity	NPC99666
0.766	Intermediate Similarity	NPC200888
0.7639	Intermediate Similarity	NPC477532
0.7637	Intermediate Similarity	NPC209174
0.7629	Intermediate Similarity	NPC473179
0.7629	Intermediate Similarity	NPC213530
0.7629	Intermediate Similarity	NPC193267
0.7611	Intermediate Similarity	NPC193777
0.76	Intermediate Similarity	NPC285558
0.76	Intermediate Similarity	NPC476581
0.76	Intermediate Similarity	NPC36229
0.76	Intermediate Similarity	NPC16452
0.7586	Intermediate Similarity	NPC469594
0.7585	Intermediate Similarity	NPC202503
0.7578	Intermediate Similarity	NPC234197
0.7573	Intermediate Similarity	NPC233334
0.7569	Intermediate Similarity	NPC76748
0.7564	Intermediate Similarity	NPC310118
0.756	Intermediate Similarity	NPC472589
0.7556	Intermediate Similarity	NPC223427
0.7534	Intermediate Similarity	NPC476578
0.7534	Intermediate Similarity	NPC4071
0.7534	Intermediate Similarity	NPC92111
0.7534	Intermediate Similarity	NPC476582
0.7531	Intermediate Similarity	NPC476999
0.7523	Intermediate Similarity	NPC296527
0.7523	Intermediate Similarity	NPC243834
0.7523	Intermediate Similarity	NPC70956
0.7522	Intermediate Similarity	NPC473180
0.7522	Intermediate Similarity	NPC202768
0.7522	Intermediate Similarity	NPC296482
0.7522	Intermediate Similarity	NPC53069
0.7522	Intermediate Similarity	NPC94157
0.7522	Intermediate Similarity	NPC96405
0.7522	Intermediate Similarity	NPC171409
0.751	Intermediate Similarity	NPC90875
0.75	Intermediate Similarity	NPC469554
0.749	Intermediate Similarity	NPC469792
0.7489	Intermediate Similarity	NPC471080
0.7489	Intermediate Similarity	NPC476106
0.7489	Intermediate Similarity	NPC469592
0.748	Intermediate Similarity	NPC472588
0.748	Intermediate Similarity	NPC78609
0.748	Intermediate Similarity	NPC124313
0.7479	Intermediate Similarity	NPC148409
0.7478	Intermediate Similarity	NPC475774
0.7467	Intermediate Similarity	NPC31930
0.7456	Intermediate Similarity	NPC313189
0.7456	Intermediate Similarity	NPC135549
0.7447	Intermediate Similarity	NPC477533
0.7446	Intermediate Similarity	NPC48353
0.7435	Intermediate Similarity	NPC290689
0.7435	Intermediate Similarity	NPC5145
0.7435	Intermediate Similarity	NPC199667
0.7432	Intermediate Similarity	NPC326634
0.743	Intermediate Similarity	NPC134637
0.7429	Intermediate Similarity	NPC210296
0.7422	Intermediate Similarity	NPC176538
0.7422	Intermediate Similarity	NPC477019
0.7421	Intermediate Similarity	NPC114335
0.7421	Intermediate Similarity	NPC280964
0.7421	Intermediate Similarity	NPC141915
0.7398	Intermediate Similarity	NPC207283
0.7398	Intermediate Similarity	NPC84164
0.7391	Intermediate Similarity	NPC473181
0.7385	Intermediate Similarity	NPC314002
0.7383	Intermediate Similarity	NPC132385
0.7368	Intermediate Similarity	NPC470500
0.7368	Intermediate Similarity	NPC475070
0.7366	Intermediate Similarity	NPC77555
0.7364	Intermediate Similarity	NPC227908
0.7364	Intermediate Similarity	NPC128751
0.7362	Intermediate Similarity	NPC284685
0.7362	Intermediate Similarity	NPC477609
0.7362	Intermediate Similarity	NPC129897
0.7359	Intermediate Similarity	NPC167860
0.7359	Intermediate Similarity	NPC123976
0.7357	Intermediate Similarity	NPC475085
0.7357	Intermediate Similarity	NPC475112
0.7357	Intermediate Similarity	NPC291535
0.7355	Intermediate Similarity	NPC101543
0.7352	Intermediate Similarity	NPC171171
0.735	Intermediate Similarity	NPC8022
0.735	Intermediate Similarity	NPC470799
0.7344	Intermediate Similarity	NPC24019
0.7339	Intermediate Similarity	NPC478074
0.7339	Intermediate Similarity	NPC474594
0.7339	Intermediate Similarity	NPC204717
0.7336	Intermediate Similarity	NPC304183
0.7336	Intermediate Similarity	NPC473187
0.7333	Intermediate Similarity	NPC191489
0.733	Intermediate Similarity	NPC469497
0.733	Intermediate Similarity	NPC106833
0.7321	Intermediate Similarity	NPC13880
0.7319	Intermediate Similarity	NPC314552
0.7318	Intermediate Similarity	NPC46580
0.7314	Intermediate Similarity	NPC475253
0.7313	Intermediate Similarity	NPC232727
0.7303	Intermediate Similarity	NPC477608
0.7303	Intermediate Similarity	NPC477607
0.7301	Intermediate Similarity	NPC128823
0.73	Intermediate Similarity	NPC86078
0.7296	Intermediate Similarity	NPC26679
0.7294	Intermediate Similarity	NPC220765
0.7293	Intermediate Similarity	NPC210256
0.7292	Intermediate Similarity	NPC214980
0.7288	Intermediate Similarity	NPC173080
0.7285	Intermediate Similarity	NPC22928
0.7277	Intermediate Similarity	NPC288349
0.7277	Intermediate Similarity	NPC131017
0.7265	Intermediate Similarity	NPC108342
0.7265	Intermediate Similarity	NPC324149
0.7265	Intermediate Similarity	NPC477610
0.7262	Intermediate Similarity	NPC473188
0.7249	Intermediate Similarity	NPC162484
0.7246	Intermediate Similarity	NPC304926
0.7246	Intermediate Similarity	NPC476041
0.7237	Intermediate Similarity	NPC267423
0.7236	Intermediate Similarity	NPC189903
0.7236	Intermediate Similarity	NPC15801
0.7236	Intermediate Similarity	NPC182907
0.7222	Intermediate Similarity	NPC294620
0.722	Intermediate Similarity	NPC88923
0.722	Intermediate Similarity	NPC100734
0.722	Intermediate Similarity	NPC315634
0.7218	Intermediate Similarity	NPC119134
0.7212	Intermediate Similarity	NPC153042
0.7212	Intermediate Similarity	NPC156704
0.7207	Intermediate Similarity	NPC246700
0.7206	Intermediate Similarity	NPC166722
0.7202	Intermediate Similarity	NPC326363
0.72	Intermediate Similarity	NPC208522
0.7198	Intermediate Similarity	NPC475910
0.7194	Intermediate Similarity	NPC302807
0.7191	Intermediate Similarity	NPC162530
0.7184	Intermediate Similarity	NPC180504
0.7181	Intermediate Similarity	NPC72211
0.7174	Intermediate Similarity	NPC469440
0.7167	Intermediate Similarity	NPC210434
0.7167	Intermediate Similarity	NPC469589
0.7167	Intermediate Similarity	NPC185782
0.7167	Intermediate Similarity	NPC201697
0.7162	Intermediate Similarity	NPC219170
0.7162	Intermediate Similarity	NPC180253
0.7156	Intermediate Similarity	NPC279401

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 NPC284141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	690
0.2-0.3	982
0.3-0.4	1861
0.4-0.5	2638
0.5-0.6	2034
0.6-0.7	572
0.7-0.8	65
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
0.8069	Intermediate Similarity	NPD7558	Phase 2
0.8069	Intermediate Similarity	NPD6494	Phase 2
0.805	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.8044	Intermediate Similarity	NPD5612	Discontinued
0.7841	Intermediate Similarity	NPD5902	Approved
0.7841	Intermediate Similarity	NPD5903	Approved
0.7783	Intermediate Similarity	NPD3763	Approved
0.7706	Intermediate Similarity	NPD1038	Approved
0.7668	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3921	Approved
0.7661	Intermediate Similarity	NPD3923	Approved
0.7661	Intermediate Similarity	NPD3922	Approved
0.7661	Intermediate Similarity	NPD3924	Approved
0.7602	Intermediate Similarity	NPD7948	Phase 1
0.7577	Intermediate Similarity	NPD5658	Approved
0.7555	Intermediate Similarity	NPD5066	Phase 2
0.7555	Intermediate Similarity	NPD5067	Phase 2
0.7545	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1392	Approved
0.7522	Intermediate Similarity	NPD3816	Phase 1
0.7522	Intermediate Similarity	NPD3815	Phase 1
0.7489	Intermediate Similarity	NPD3003	Approved
0.7466	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4502	Phase 2
0.7381	Intermediate Similarity	NPD8442	Discontinued
0.7378	Intermediate Similarity	NPD3825	Phase 3
0.7375	Intermediate Similarity	NPD7555	Discontinued
0.7362	Intermediate Similarity	NPD7955	Approved
0.7362	Intermediate Similarity	NPD7956	Approved
0.736	Intermediate Similarity	NPD6243	Phase 3
0.736	Intermediate Similarity	NPD6244	Phase 3
0.7357	Intermediate Similarity	NPD6975	Discontinued
0.7333	Intermediate Similarity	NPD7708	Approved
0.7323	Intermediate Similarity	NPD7169	Suspended
0.7319	Intermediate Similarity	NPD5164	Discontinued
0.7304	Intermediate Similarity	NPD7453	Approved
0.7304	Intermediate Similarity	NPD7452	Approved
0.7304	Intermediate Similarity	NPD7222	Phase 2
0.7295	Intermediate Similarity	NPD6964	Approved
0.7295	Intermediate Similarity	NPD6963	Approved
0.7273	Intermediate Similarity	NPD7567	Approved
0.7258	Intermediate Similarity	NPD6473	Phase 1
0.7254	Intermediate Similarity	NPD4080	Discontinued
0.7225	Intermediate Similarity	NPD1768	Approved
0.722	Intermediate Similarity	NPD7803	Approved
0.7215	Intermediate Similarity	NPD6985	Discontinued
0.7179	Intermediate Similarity	NPD5936	Approved
0.7179	Intermediate Similarity	NPD5939	Approved
0.7171	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7859	Phase 2
0.7156	Intermediate Similarity	NPD3920	Phase 2
0.7156	Intermediate Similarity	NPD6361	Phase 2
0.7155	Intermediate Similarity	NPD6242	Discontinued
0.7154	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7069	Discontinued
0.7143	Intermediate Similarity	NPD4038	Approved
0.7143	Intermediate Similarity	NPD4035	Approved
0.7143	Intermediate Similarity	NPD4037	Approved
0.7143	Intermediate Similarity	NPD4039	Approved
0.7143	Intermediate Similarity	NPD4885	Approved
0.7143	Intermediate Similarity	NPD4033	Approved
0.7143	Intermediate Similarity	NPD31	Approved
0.7143	Intermediate Similarity	NPD4034	Approved
0.7143	Intermediate Similarity	NPD32	Approved
0.7143	Intermediate Similarity	NPD4036	Approved
0.7143	Intermediate Similarity	NPD4122	Approved
0.7132	Intermediate Similarity	NPD6531	Approved
0.7132	Intermediate Similarity	NPD6530	Approved
0.7131	Intermediate Similarity	NPD8512	Phase 3
0.7124	Intermediate Similarity	NPD2187	Approved
0.7124	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2189	Approved
0.712	Intermediate Similarity	NPD4875	Phase 3
0.712	Intermediate Similarity	NPD4876	Phase 3
0.7119	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4375	Approved
0.7113	Intermediate Similarity	NPD7194	Discontinued
0.7101	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3386	Phase 2
0.7087	Intermediate Similarity	NPD4511	Phase 1
0.7085	Intermediate Similarity	NPD8431	Approved
0.7083	Intermediate Similarity	NPD5930	Phase 3
0.7078	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6230	Discontinued
0.7056	Intermediate Similarity	NPD4454	Phase 2
0.7054	Intermediate Similarity	NPD8091	Phase 3
0.7046	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6595	Phase 3
0.7034	Intermediate Similarity	NPD6220	Phase 3
0.702	Intermediate Similarity	NPD5482	Discontinued
0.7012	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7417	Discontinued
0.7009	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD802	Phase 2
0.6996	Remote Similarity	NPD4349	Approved
0.6996	Remote Similarity	NPD4350	Approved
0.6984	Remote Similarity	NPD6517	Phase 3
0.6976	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8403	Phase 1
0.6966	Remote Similarity	NPD5530	Phase 1
0.6962	Remote Similarity	NPD4131	Phase 3
0.6955	Remote Similarity	NPD1954	Phase 1
0.6955	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5559	Phase 2
0.6951	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4437	Phase 3
0.6943	Remote Similarity	NPD8364	Approved
0.6943	Remote Similarity	NPD8363	Approved
0.6936	Remote Similarity	NPD6290	Phase 2
0.6929	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD2176	Approved
0.6926	Remote Similarity	NPD2175	Phase 3
0.6926	Remote Similarity	NPD8395	Approved
0.6926	Remote Similarity	NPD8396	Approved
0.6926	Remote Similarity	NPD2177	Approved
0.6923	Remote Similarity	NPD4795	Phase 2
0.692	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1483	Discontinued
0.6911	Remote Similarity	NPD6978	Phase 2
0.6911	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6455	Phase 3
0.69	Remote Similarity	NPD4418	Discontinued
0.69	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD484	Approved
0.6891	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7470	Discontinued
0.6872	Remote Similarity	NPD6856	Discontinued
0.6872	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7674	Phase 3
0.687	Remote Similarity	NPD7675	Phase 3
0.6868	Remote Similarity	NPD7673	Phase 3
0.6865	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5065	Approved
0.6862	Remote Similarity	NPD3330	Phase 1
0.686	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8016	Phase 3
0.6838	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3402	Phase 1
0.683	Remote Similarity	NPD8284	Discontinued
0.6829	Remote Similarity	NPD7719	Discontinued
0.6829	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7689	Approved
0.6824	Remote Similarity	NPD1739	Approved
0.6824	Remote Similarity	NPD1740	Approved
0.6822	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1856	Discontinued
0.6812	Remote Similarity	NPD6569	Phase 2
0.6811	Remote Similarity	NPD3872	Phase 3
0.6809	Remote Similarity	NPD8358	Approved
0.6808	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7603	Discontinued
0.6802	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6801	Remote Similarity	NPD7181	Phase 3
0.6797	Remote Similarity	NPD6745	Discontinued
0.6792	Remote Similarity	NPD6456	Discontinued
0.679	Remote Similarity	NPD8465	Approved
0.679	Remote Similarity	NPD8428	Approved
0.679	Remote Similarity	NPD8467	Approved
0.679	Remote Similarity	NPD3354	Phase 2
0.679	Remote Similarity	NPD8466	Approved
0.679	Remote Similarity	NPD8429	Approved
0.679	Remote Similarity	NPD8427	Approved
0.6787	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4551	Phase 2
0.678	Remote Similarity	NPD3397	Phase 2
0.6777	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD6723	Discontinued
0.6773	Remote Similarity	NPD4083	Discontinued
0.6767	Remote Similarity	NPD3343	Phase 3
0.6765	Remote Similarity	NPD7672	Approved
0.6765	Remote Similarity	NPD7671	Approved
0.6765	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD8524	Approved
0.6762	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3875	Discontinued
0.6759	Remote Similarity	NPD4343	Phase 1
0.6759	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4021	Phase 2
0.675	Remote Similarity	NPD949	Phase 1
0.6748	Remote Similarity	NPD7221	Approved
0.6748	Remote Similarity	NPD7219	Approved
0.6734	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7051	Phase 3
0.6734	Remote Similarity	NPD7426	Phase 1
0.6727	Remote Similarity	NPD1326	Approved
0.6727	Remote Similarity	NPD1325	Approved
0.6726	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6281	Approved
0.6723	Remote Similarity	NPD5429	Discontinued
0.6722	Remote Similarity	NPD8093	Discontinued

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