NPASS Compound

Structure

NPC217554 OpenBabel07101718242D 34 38 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 2.3675 3.9236 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 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 -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 17 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 18 2 0 0 0 0 10 19 2 0 0 0 0 11 23 2 0 0 0 0 12 24 2 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 15 30 1 0 0 0 0 16 22 2 0 0 0 0 16 31 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 32 1 0 0 0 0 28 33 1 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.21
Volume:	484.084
LogP:	6.985
LogD:	4.404
LogS:	-3.449
# Rotatable Bonds:	6
TPSA:	70.27
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	2.911
Fsp3:	0.172
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.358
MDCK Permeability:	9.188960575556848e-06
Pgp-inhibitor:	0.998
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	94.92749786376953%
Volume Distribution (VD):	1.641
Pgp-substrate:	1.6722536087036133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.838
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.979
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.945
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.593
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.703
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	4.171
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.568
Human Hepatotoxicity (H-HT):	0.8
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.28
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.472

Download Data

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

Natural Product: NPC217554

Natural Product ID:	NPC217554
*Common Name:**	Ochrindole A
IUPAC Name:	2,5-bis(1H-indol-3-yl)-3,6-dimethoxy-4-(3-methylbut-2-enyl)phenol
Synonyms:
Standard InCHIKey:	YVQFFNCNPFQQKW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H28N2O3/c1-17(2)13-14-20-25(21-15-30-23-11-7-5-9-18(21)23)29(34-4)27(32)26(28(20)33-3)22-16-31-24-12-8-6-10-19(22)24/h5-13,15-16,30-32H,14H2,1-4H3
SMILES:	COc1c(c(O)c(c(c1CC=C(C)C)c1c[nH]c2c1cccc2)OC)c1c[nH]c2c1cccc2
Synthetic Gene Cluster:	BGC0001712;
ChEMBL Identifier:	CHEMBL479915
PubChem CID:	10004010
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	3

Activity Type	# Activity
Organism	3

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[471339]
NPT915	Organism	Helicoverpa zea	Helicoverpa zea	Activity	=	30.0	%	PMID[471339]
NPT4733	Organism	Carpophilus	Carpophilus	Activity	=	20.0	%	PMID[471339]

☑ 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 NPC217554 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	657
0.1-0.2	3537
0.2-0.3	13346
0.3-0.4	4879
0.4-0.5	12397
0.5-0.6	5547
0.6-0.7	1966
0.7-0.8	343
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9906	High Similarity	NPC11408
0.986	High Similarity	NPC284141
0.8565	High Similarity	NPC266931
0.8507	High Similarity	NPC122463
0.8416	Intermediate Similarity	NPC174049
0.8265	Intermediate Similarity	NPC316981
0.8225	Intermediate Similarity	NPC473183
0.8217	Intermediate Similarity	NPC473184
0.8174	Intermediate Similarity	NPC255800
0.8174	Intermediate Similarity	NPC96584
0.8161	Intermediate Similarity	NPC473822
0.8103	Intermediate Similarity	NPC295228
0.8097	Intermediate Similarity	NPC118121
0.8095	Intermediate Similarity	NPC473182
0.8087	Intermediate Similarity	NPC201508
0.808	Intermediate Similarity	NPC204446
0.8079	Intermediate Similarity	NPC476997
0.8072	Intermediate Similarity	NPC170114
0.8054	Intermediate Similarity	NPC208284
0.8043	Intermediate Similarity	NPC476998
0.8043	Intermediate Similarity	NPC476996
0.8027	Intermediate Similarity	NPC470549
0.8	Intermediate Similarity	NPC476994
0.7983	Intermediate Similarity	NPC277351
0.7937	Intermediate Similarity	NPC202605
0.7937	Intermediate Similarity	NPC112206
0.7928	Intermediate Similarity	NPC11464
0.7879	Intermediate Similarity	NPC473185
0.786	Intermediate Similarity	NPC280272
0.7854	Intermediate Similarity	NPC135887
0.7854	Intermediate Similarity	NPC199277
0.7824	Intermediate Similarity	NPC15406
0.7814	Intermediate Similarity	NPC307963
0.7807	Intermediate Similarity	NPC46451
0.7788	Intermediate Similarity	NPC224928
0.7788	Intermediate Similarity	NPC235076
0.7778	Intermediate Similarity	NPC251160
0.7773	Intermediate Similarity	NPC89549
0.7773	Intermediate Similarity	NPC132642
0.7768	Intermediate Similarity	NPC252251
0.7768	Intermediate Similarity	NPC188420
0.7767	Intermediate Similarity	NPC99666
0.7764	Intermediate Similarity	NPC476995
0.7763	Intermediate Similarity	NPC100079
0.7763	Intermediate Similarity	NPC23614
0.7743	Intermediate Similarity	NPC149471
0.7743	Intermediate Similarity	NPC271215
0.7742	Intermediate Similarity	NPC251090
0.7729	Intermediate Similarity	NPC193267
0.7729	Intermediate Similarity	NPC473179
0.7729	Intermediate Similarity	NPC213530
0.7713	Intermediate Similarity	NPC193777
0.7705	Intermediate Similarity	NPC183537
0.7705	Intermediate Similarity	NPC77878
0.7703	Intermediate Similarity	NPC285558
0.7702	Intermediate Similarity	NPC477531
0.7685	Intermediate Similarity	NPC133140
0.7685	Intermediate Similarity	NPC195268
0.7682	Intermediate Similarity	NPC234197
0.7682	Intermediate Similarity	NPC200888
0.7674	Intermediate Similarity	NPC76748
0.7662	Intermediate Similarity	NPC477532
0.7662	Intermediate Similarity	NPC310118
0.766	Intermediate Similarity	NPC209174
0.7658	Intermediate Similarity	NPC223427
0.765	Intermediate Similarity	NPC110151
0.7639	Intermediate Similarity	NPC92111
0.7628	Intermediate Similarity	NPC296527
0.7626	Intermediate Similarity	NPC70956
0.7626	Intermediate Similarity	NPC243834
0.7623	Intermediate Similarity	NPC16452
0.7623	Intermediate Similarity	NPC476581
0.7623	Intermediate Similarity	NPC36229
0.7621	Intermediate Similarity	NPC94157
0.7621	Intermediate Similarity	NPC473180
0.7607	Intermediate Similarity	NPC202503
0.7595	Intermediate Similarity	NPC233334
0.7581	Intermediate Similarity	NPC472589
0.7578	Intermediate Similarity	NPC475774
0.7557	Intermediate Similarity	NPC476578
0.7557	Intermediate Similarity	NPC476582
0.7557	Intermediate Similarity	NPC4071
0.7545	Intermediate Similarity	NPC137929
0.7545	Intermediate Similarity	NPC164374
0.7544	Intermediate Similarity	NPC171409
0.7544	Intermediate Similarity	NPC53069
0.7544	Intermediate Similarity	NPC96405
0.7544	Intermediate Similarity	NPC202768
0.7544	Intermediate Similarity	NPC48353
0.7544	Intermediate Similarity	NPC296482
0.7534	Intermediate Similarity	NPC326634
0.7533	Intermediate Similarity	NPC199667
0.7531	Intermediate Similarity	NPC90875
0.7523	Intermediate Similarity	NPC141915
0.7523	Intermediate Similarity	NPC176538
0.7523	Intermediate Similarity	NPC114335
0.7523	Intermediate Similarity	NPC280964
0.7523	Intermediate Similarity	NPC477019
0.7521	Intermediate Similarity	NPC469554
0.7511	Intermediate Similarity	NPC469792
0.75	Intermediate Similarity	NPC148409
0.75	Intermediate Similarity	NPC124313
0.75	Intermediate Similarity	NPC78609
0.75	Intermediate Similarity	NPC472588
0.7489	Intermediate Similarity	NPC473181
0.7489	Intermediate Similarity	NPC31930
0.7488	Intermediate Similarity	NPC314002
0.7479	Intermediate Similarity	NPC476999
0.7478	Intermediate Similarity	NPC135549
0.7478	Intermediate Similarity	NPC313189
0.7468	Intermediate Similarity	NPC477533
0.7467	Intermediate Similarity	NPC475070
0.7466	Intermediate Similarity	NPC77555
0.7465	Intermediate Similarity	NPC128751
0.7458	Intermediate Similarity	NPC227908
0.7457	Intermediate Similarity	NPC469594
0.7457	Intermediate Similarity	NPC477609
0.7456	Intermediate Similarity	NPC290689
0.7456	Intermediate Similarity	NPC123976
0.7456	Intermediate Similarity	NPC167860
0.7455	Intermediate Similarity	NPC475085
0.7455	Intermediate Similarity	NPC291535
0.7455	Intermediate Similarity	NPC475112
0.7454	Intermediate Similarity	NPC171171
0.7449	Intermediate Similarity	NPC134637
0.7449	Intermediate Similarity	NPC210296
0.7448	Intermediate Similarity	NPC101543
0.7446	Intermediate Similarity	NPC8022
0.7446	Intermediate Similarity	NPC470799
0.7442	Intermediate Similarity	NPC204717
0.7435	Intermediate Similarity	NPC469592
0.7435	Intermediate Similarity	NPC471080
0.7435	Intermediate Similarity	NPC478074
0.7434	Intermediate Similarity	NPC476106
0.7431	Intermediate Similarity	NPC469497
0.7431	Intermediate Similarity	NPC106833
0.7421	Intermediate Similarity	NPC13880
0.7419	Intermediate Similarity	NPC46580
0.7418	Intermediate Similarity	NPC84164
0.7418	Intermediate Similarity	NPC207283
0.7411	Intermediate Similarity	NPC232727
0.7406	Intermediate Similarity	NPC475253
0.7402	Intermediate Similarity	NPC132385
0.7395	Intermediate Similarity	NPC220765
0.7395	Intermediate Similarity	NPC477608
0.7395	Intermediate Similarity	NPC477607
0.7393	Intermediate Similarity	NPC86078
0.7382	Intermediate Similarity	NPC173080
0.7381	Intermediate Similarity	NPC129897
0.738	Intermediate Similarity	NPC5145
0.7376	Intermediate Similarity	NPC131017
0.7364	Intermediate Similarity	NPC324149
0.7364	Intermediate Similarity	NPC24019
0.7359	Intermediate Similarity	NPC477610
0.7357	Intermediate Similarity	NPC304183
0.7345	Intermediate Similarity	NPC162484
0.7339	Intermediate Similarity	NPC304926
0.7339	Intermediate Similarity	NPC476041
0.7333	Intermediate Similarity	NPC267423
0.7316	Intermediate Similarity	NPC26679
0.7316	Intermediate Similarity	NPC294620
0.7313	Intermediate Similarity	NPC210256
0.7313	Intermediate Similarity	NPC470500
0.7312	Intermediate Similarity	NPC284685
0.7311	Intermediate Similarity	NPC214980
0.7309	Intermediate Similarity	NPC153042
0.7306	Intermediate Similarity	NPC22928
0.7306	Intermediate Similarity	NPC246700
0.7284	Intermediate Similarity	NPC108342
0.7284	Intermediate Similarity	NPC473187
0.7284	Intermediate Similarity	NPC162530
0.7283	Intermediate Similarity	NPC191489
0.7277	Intermediate Similarity	NPC72211
0.7261	Intermediate Similarity	NPC201697
0.7261	Intermediate Similarity	NPC185782
0.7257	Intermediate Similarity	NPC210434
0.7254	Intermediate Similarity	NPC182907
0.7254	Intermediate Similarity	NPC15801
0.7254	Intermediate Similarity	NPC189903
0.7244	Intermediate Similarity	NPC128823
0.7236	Intermediate Similarity	NPC119134
0.7235	Intermediate Similarity	NPC176127
0.7234	Intermediate Similarity	NPC264285
0.7232	Intermediate Similarity	NPC156704
0.7224	Intermediate Similarity	NPC166722
0.722	Intermediate Similarity	NPC205934
0.722	Intermediate Similarity	NPC43787
0.722	Intermediate Similarity	NPC326363
0.7218	Intermediate Similarity	NPC208522
0.7217	Intermediate Similarity	NPC476465
0.7215	Intermediate Similarity	NPC60621
0.7211	Intermediate Similarity	NPC302807
0.7211	Intermediate Similarity	NPC473188
0.721	Intermediate Similarity	NPC474594
0.7209	Intermediate Similarity	NPC184964
0.7202	Intermediate Similarity	NPC190007
0.7202	Intermediate Similarity	NPC180504
0.72	Intermediate Similarity	NPC91868
0.72	Intermediate Similarity	NPC63971
0.7193	Intermediate Similarity	NPC469440

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 NPC217554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	712
0.2-0.3	949
0.3-0.4	1848
0.4-0.5	2671
0.5-0.6	2003
0.6-0.7	571
0.7-0.8	67
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
0.8075	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD6494	Phase 2
0.7991	Intermediate Similarity	NPD5612	Discontinued
0.794	Intermediate Similarity	NPD7558	Phase 2
0.7814	Intermediate Similarity	NPD1038	Approved
0.7807	Intermediate Similarity	NPD3763	Approved
0.7709	Intermediate Similarity	NPD5902	Approved
0.7709	Intermediate Similarity	NPD5903	Approved
0.7689	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD3921	Approved
0.7685	Intermediate Similarity	NPD3924	Approved
0.7685	Intermediate Similarity	NPD3922	Approved
0.7685	Intermediate Similarity	NPD3923	Approved
0.7679	Intermediate Similarity	NPD5658	Approved
0.765	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7948	Phase 1
0.7569	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3816	Phase 1
0.7544	Intermediate Similarity	NPD3815	Phase 1
0.75	Intermediate Similarity	NPD5066	Phase 2
0.75	Intermediate Similarity	NPD5067	Phase 2
0.7478	Intermediate Similarity	NPD1392	Approved
0.7455	Intermediate Similarity	NPD6975	Discontinued
0.7434	Intermediate Similarity	NPD3003	Approved
0.7399	Intermediate Similarity	NPD3825	Phase 3
0.7395	Intermediate Similarity	NPD7555	Discontinued
0.7379	Intermediate Similarity	NPD6243	Phase 3
0.7379	Intermediate Similarity	NPD6244	Phase 3
0.7341	Intermediate Similarity	NPD7169	Suspended
0.7325	Intermediate Similarity	NPD7452	Approved
0.7325	Intermediate Similarity	NPD7222	Phase 2
0.7325	Intermediate Similarity	NPD7453	Approved
0.7314	Intermediate Similarity	NPD6964	Approved
0.7314	Intermediate Similarity	NPD6963	Approved
0.7312	Intermediate Similarity	NPD7955	Approved
0.7312	Intermediate Similarity	NPD7956	Approved
0.7283	Intermediate Similarity	NPD7708	Approved
0.7273	Intermediate Similarity	NPD4502	Phase 2
0.7269	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD8442	Discontinued
0.7256	Intermediate Similarity	NPD3920	Phase 2
0.7252	Intermediate Similarity	NPD6361	Phase 2
0.7248	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6242	Discontinued
0.7244	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7567	Approved
0.7217	Intermediate Similarity	NPD2189	Approved
0.7217	Intermediate Similarity	NPD2187	Approved
0.7216	Intermediate Similarity	NPD6530	Approved
0.7216	Intermediate Similarity	NPD6531	Approved
0.7215	Intermediate Similarity	NPD4375	Approved
0.7206	Intermediate Similarity	NPD6473	Phase 1
0.7202	Intermediate Similarity	NPD4080	Discontinued
0.7191	Intermediate Similarity	NPD5164	Discontinued
0.7191	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD3386	Phase 2
0.7181	Intermediate Similarity	NPD4511	Phase 1
0.7176	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5930	Phase 3
0.7171	Intermediate Similarity	NPD7803	Approved
0.7168	Intermediate Similarity	NPD1768	Approved
0.7161	Intermediate Similarity	NPD6985	Discontinued
0.716	Intermediate Similarity	NPD4885	Approved
0.7143	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD4875	Phase 3
0.7137	Intermediate Similarity	NPD4876	Phase 3
0.7137	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5939	Approved
0.7124	Intermediate Similarity	NPD5936	Approved
0.7121	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7859	Phase 2
0.7104	Intermediate Similarity	NPD8431	Approved
0.7103	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7069	Discontinued
0.7089	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4035	Approved
0.7087	Intermediate Similarity	NPD4122	Approved
0.7087	Intermediate Similarity	NPD4037	Approved
0.7087	Intermediate Similarity	NPD4036	Approved
0.7087	Intermediate Similarity	NPD4034	Approved
0.7087	Intermediate Similarity	NPD4038	Approved
0.7087	Intermediate Similarity	NPD32	Approved
0.7087	Intermediate Similarity	NPD31	Approved
0.7087	Intermediate Similarity	NPD4039	Approved
0.7087	Intermediate Similarity	NPD4033	Approved
0.708	Intermediate Similarity	NPD6230	Discontinued
0.707	Intermediate Similarity	NPD8091	Phase 3
0.7066	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6595	Phase 3
0.7061	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7194	Discontinued
0.7056	Intermediate Similarity	NPD5530	Phase 1
0.7051	Intermediate Similarity	NPD6220	Phase 3
0.7051	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1954	Phase 1
0.7029	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD802	Phase 2
0.7014	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4795	Phase 2
0.7012	Intermediate Similarity	NPD4349	Approved
0.7012	Intermediate Similarity	NPD4350	Approved
0.7008	Intermediate Similarity	NPD8512	Phase 3
0.7004	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD484	Approved
0.6983	Remote Similarity	NPD8403	Phase 1
0.6969	Remote Similarity	NPD5482	Discontinued
0.6967	Remote Similarity	NPD5559	Phase 2
0.6966	Remote Similarity	NPD4437	Phase 3
0.6966	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7417	Discontinued
0.6959	Remote Similarity	NPD5065	Approved
0.6958	Remote Similarity	NPD6856	Discontinued
0.6943	Remote Similarity	NPD8396	Approved
0.6943	Remote Similarity	NPD8395	Approved
0.6935	Remote Similarity	NPD4454	Phase 2
0.6932	Remote Similarity	NPD1483	Discontinued
0.6916	Remote Similarity	NPD4418	Discontinued
0.6916	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1740	Approved
0.6913	Remote Similarity	NPD1739	Approved
0.6907	Remote Similarity	NPD4131	Phase 3
0.6901	Remote Similarity	NPD1856	Discontinued
0.6898	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3872	Phase 3
0.6882	Remote Similarity	NPD7673	Phase 3
0.6878	Remote Similarity	NPD3330	Phase 1
0.6877	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4551	Phase 2
0.687	Remote Similarity	NPD2176	Approved
0.687	Remote Similarity	NPD2177	Approved
0.687	Remote Similarity	NPD2175	Phase 3
0.6865	Remote Similarity	NPD6517	Phase 3
0.6853	Remote Similarity	NPD8016	Phase 3
0.6853	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7672	Approved
0.6851	Remote Similarity	NPD7671	Approved
0.6846	Remote Similarity	NPD3402	Phase 1
0.6844	Remote Similarity	NPD8284	Discontinued
0.6844	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7689	Approved
0.6838	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD949	Phase 1
0.6835	Remote Similarity	NPD7470	Discontinued
0.6831	Remote Similarity	NPD7219	Approved
0.6831	Remote Similarity	NPD7221	Approved
0.683	Remote Similarity	NPD8363	Approved
0.683	Remote Similarity	NPD8364	Approved
0.6828	Remote Similarity	NPD6569	Phase 2
0.6824	Remote Similarity	NPD8358	Approved
0.6822	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.682	Remote Similarity	NPD1325	Approved
0.682	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.682	Remote Similarity	NPD1326	Approved
0.6818	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7674	Phase 3
0.6816	Remote Similarity	NPD7603	Discontinued
0.6816	Remote Similarity	NPD7675	Phase 3
0.6813	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6745	Discontinued
0.6809	Remote Similarity	NPD6290	Phase 2
0.6807	Remote Similarity	NPD8093	Discontinued
0.6805	Remote Similarity	NPD3354	Phase 2
0.6803	Remote Similarity	NPD6306	Phase 2
0.6802	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3397	Phase 2
0.6795	Remote Similarity	NPD5426	Phase 3
0.6792	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4083	Discontinued
0.6789	Remote Similarity	NPD6978	Phase 2
0.6789	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD8094	Discontinued
0.6777	Remote Similarity	NPD6455	Phase 3
0.6777	Remote Similarity	NPD3875	Discontinued
0.6777	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7719	Discontinued
0.6774	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4021	Phase 2
0.6766	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6633	Phase 2
0.6749	Remote Similarity	NPD6634	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7051	Phase 3
0.6741	Remote Similarity	NPD8466	Approved
0.6741	Remote Similarity	NPD8428	Approved
0.6741	Remote Similarity	NPD8465	Approved
0.6741	Remote Similarity	NPD8427	Approved
0.6741	Remote Similarity	NPD8467	Approved
0.6741	Remote Similarity	NPD8429	Approved
0.674	Remote Similarity	NPD6281	Approved
0.6737	Remote Similarity	NPD5429	Discontinued
0.6736	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5632	Approved
0.6733	Remote Similarity	NPD3006	Discontinued
0.6732	Remote Similarity	NPD7392	Phase 2

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