NPASS Compound

Structure

NPC473187 OpenBabel07101718292D 34 39 0 0 0 0 0 0 0 0999 V2000 1.9444 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4355 -0.2909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4355 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5695 -0.7909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5695 1.2091 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 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3457 -1.5135 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 -1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3511 -1.6180 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 4.7035 -0.2909 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 3.7524 -0.6000 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 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7035 0.7091 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 2.1701 0.1045 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 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1646 0.2091 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 1.7634 -0.8090 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 3.7524 1.0181 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 -2.6831 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7688 -0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 34 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 2 0 0 0 0 7 20 2 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 31 2 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 24 2 0 0 0 0 17 25 2 0 0 0 0 18 26 2 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 29 1 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 22 27 2 0 0 0 0 23 26 1 0 0 0 0 23 28 2 0 0 0 0 24 30 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 32 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.16
Volume:	464.386
LogP:	6.442
LogD:	3.629
LogS:	-5.122
# Rotatable Bonds:	3
TPSA:	98.34
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	3.038
Fsp3:	0.107
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.012
MDCK Permeability:	7.117013410606887e-06
Pgp-inhibitor:	0.137
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.442
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.811

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	96.50340270996094%
Volume Distribution (VD):	0.341
Pgp-substrate:	3.7908785343170166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.773
CYP2C9-substrate:	0.69
CYP2D6-inhibitor:	0.33
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.125
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	2.958
Half-life (T1/2):	0.095

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.722
Rat Oral Acute Toxicity:	0.762
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.906
Carcinogencity:	0.622
Eye Corrosion:	0.003
Eye Irritation:	0.899
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC473187

Natural Product ID:	NPC473187
*Common Name:**	CAVZOIPWOMKMEX-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CAVZOIPWOMKMEX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H22N2O4/c1-13-10-17-15-6-4-5-7-20(15)29-25(17)22(27(13)32)23-26-18(11-14(2)28(23)33)16-8-9-21(34-3)19(12-31)24(16)30-26/h4-12,29-30,32-33H,1-3H3
SMILES:	CC1=CC2=C(C(=C1O)C3=C(C(=CC4=C3NC5=CC=CC=C54)C)O)NC6=C2C=CC(=C6C=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633083
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33199	murraya tetramera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26327273]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Activity	<	80.0	%	PMID[484330]

☑ 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 NPC473187 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	469
0.1-0.2	2605
0.2-0.3	12717
0.3-0.4	4626
0.4-0.5	13102
0.5-0.6	6942
0.6-0.7	1739
0.7-0.8	442
0.8-0.85	32
0.85-0.9	19
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9107	High Similarity	NPC473188
0.91	High Similarity	NPC150239
0.9005	High Similarity	NPC247803
0.8913	High Similarity	NPC89549
0.8768	High Similarity	NPC310211
0.8768	High Similarity	NPC308137
0.872	High Similarity	NPC23294
0.8704	High Similarity	NPC198503
0.8673	High Similarity	NPC303951
0.8657	High Similarity	NPC174760
0.8651	High Similarity	NPC46561
0.8618	High Similarity	NPC477532
0.8616	High Similarity	NPC6786
0.8578	High Similarity	NPC86834
0.8578	High Similarity	NPC210828
0.8531	High Similarity	NPC249583
0.8519	High Similarity	NPC169402
0.8472	Intermediate Similarity	NPC3207
0.8458	Intermediate Similarity	NPC87413
0.844	Intermediate Similarity	NPC473179
0.8426	Intermediate Similarity	NPC116238
0.8386	Intermediate Similarity	NPC252251
0.8365	Intermediate Similarity	NPC243834
0.8365	Intermediate Similarity	NPC70956
0.8333	Intermediate Similarity	NPC179287
0.8318	Intermediate Similarity	NPC39679
0.8311	Intermediate Similarity	NPC477531
0.8283	Intermediate Similarity	NPC91868
0.8283	Intermediate Similarity	NPC63971
0.8271	Intermediate Similarity	NPC4687
0.8267	Intermediate Similarity	NPC209174
0.8259	Intermediate Similarity	NPC473185
0.8202	Intermediate Similarity	NPC39370
0.8194	Intermediate Similarity	NPC473186
0.8169	Intermediate Similarity	NPC291535
0.8169	Intermediate Similarity	NPC475085
0.8169	Intermediate Similarity	NPC475112
0.8153	Intermediate Similarity	NPC477533
0.814	Intermediate Similarity	NPC476106
0.814	Intermediate Similarity	NPC45190
0.8108	Intermediate Similarity	NPC208084
0.8102	Intermediate Similarity	NPC193777
0.8053	Intermediate Similarity	NPC202503
0.8037	Intermediate Similarity	NPC9894
0.8	Intermediate Similarity	NPC473182
0.7981	Intermediate Similarity	NPC72211
0.7974	Intermediate Similarity	NPC473183
0.7966	Intermediate Similarity	NPC475666
0.7957	Intermediate Similarity	NPC132329
0.794	Intermediate Similarity	NPC101350
0.7925	Intermediate Similarity	NPC131017
0.7924	Intermediate Similarity	NPC81939
0.7919	Intermediate Similarity	NPC48353
0.7911	Intermediate Similarity	NPC132642
0.7904	Intermediate Similarity	NPC194740
0.7897	Intermediate Similarity	NPC235685
0.789	Intermediate Similarity	NPC300156
0.7888	Intermediate Similarity	NPC277351
0.7888	Intermediate Similarity	NPC473184
0.7887	Intermediate Similarity	NPC70259
0.7885	Intermediate Similarity	NPC94943
0.788	Intermediate Similarity	NPC162484
0.784	Intermediate Similarity	NPC43787
0.784	Intermediate Similarity	NPC205934
0.7837	Intermediate Similarity	NPC190007
0.7832	Intermediate Similarity	NPC225279
0.7826	Intermediate Similarity	NPC274640
0.7826	Intermediate Similarity	NPC471762
0.7822	Intermediate Similarity	NPC184408
0.7798	Intermediate Similarity	NPC134848
0.7797	Intermediate Similarity	NPC280799
0.7793	Intermediate Similarity	NPC187501
0.7788	Intermediate Similarity	NPC212535
0.7788	Intermediate Similarity	NPC267423
0.7773	Intermediate Similarity	NPC78609
0.7759	Intermediate Similarity	NPC475253
0.7758	Intermediate Similarity	NPC12344
0.7748	Intermediate Similarity	NPC199667
0.7743	Intermediate Similarity	NPC473041
0.7743	Intermediate Similarity	NPC303658
0.7733	Intermediate Similarity	NPC132385
0.7733	Intermediate Similarity	NPC170114
0.7729	Intermediate Similarity	NPC122436
0.7729	Intermediate Similarity	NPC51388
0.7717	Intermediate Similarity	NPC223427
0.7712	Intermediate Similarity	NPC470784
0.7706	Intermediate Similarity	NPC476044
0.7705	Intermediate Similarity	NPC472589
0.7703	Intermediate Similarity	NPC201697
0.7703	Intermediate Similarity	NPC473181
0.7699	Intermediate Similarity	NPC208522
0.7699	Intermediate Similarity	NPC293151
0.7696	Intermediate Similarity	NPC97746
0.7695	Intermediate Similarity	NPC472588
0.7692	Intermediate Similarity	NPC183777
0.7689	Intermediate Similarity	NPC470549
0.7689	Intermediate Similarity	NPC118228
0.7686	Intermediate Similarity	NPC144452
0.7685	Intermediate Similarity	NPC153042
0.7679	Intermediate Similarity	NPC473180
0.7679	Intermediate Similarity	NPC94157
0.7672	Intermediate Similarity	NPC66777
0.7669	Intermediate Similarity	NPC184680
0.7665	Intermediate Similarity	NPC264285
0.7664	Intermediate Similarity	NPC478080
0.7655	Intermediate Similarity	NPC330009
0.7655	Intermediate Similarity	NPC148183
0.7655	Intermediate Similarity	NPC152768
0.7647	Intermediate Similarity	NPC475844
0.7644	Intermediate Similarity	NPC471080
0.7644	Intermediate Similarity	NPC469592
0.7644	Intermediate Similarity	NPC39500
0.7638	Intermediate Similarity	NPC237901
0.7638	Intermediate Similarity	NPC195788
0.7637	Intermediate Similarity	NPC470785
0.7634	Intermediate Similarity	NPC294375
0.7625	Intermediate Similarity	NPC160898
0.7623	Intermediate Similarity	NPC209769
0.7623	Intermediate Similarity	NPC244543
0.7621	Intermediate Similarity	NPC305984
0.7617	Intermediate Similarity	NPC473105
0.7613	Intermediate Similarity	NPC283117
0.7613	Intermediate Similarity	NPC67401
0.7607	Intermediate Similarity	NPC474688
0.7607	Intermediate Similarity	NPC474701
0.7591	Intermediate Similarity	NPC135887
0.7591	Intermediate Similarity	NPC199277
0.7589	Intermediate Similarity	NPC11464
0.7588	Intermediate Similarity	NPC469594
0.7588	Intermediate Similarity	NPC260909
0.7578	Intermediate Similarity	NPC475910
0.7578	Intermediate Similarity	NPC470931
0.7561	Intermediate Similarity	NPC478083
0.7559	Intermediate Similarity	NPC471303
0.7555	Intermediate Similarity	NPC193267
0.7555	Intermediate Similarity	NPC213530
0.7547	Intermediate Similarity	NPC473189
0.7534	Intermediate Similarity	NPC128823
0.7532	Intermediate Similarity	NPC16352
0.7532	Intermediate Similarity	NPC260434
0.7523	Intermediate Similarity	NPC285558
0.7522	Intermediate Similarity	NPC86078
0.7522	Intermediate Similarity	NPC276657
0.7522	Intermediate Similarity	NPC294620
0.7522	Intermediate Similarity	NPC323969
0.7521	Intermediate Similarity	NPC469734
0.7511	Intermediate Similarity	NPC471304
0.751	Intermediate Similarity	NPC189079
0.75	Intermediate Similarity	NPC84478
0.75	Intermediate Similarity	NPC477066
0.75	Intermediate Similarity	NPC329747
0.7489	Intermediate Similarity	NPC60621
0.7479	Intermediate Similarity	NPC478078
0.7479	Intermediate Similarity	NPC157931
0.7478	Intermediate Similarity	NPC298436
0.7469	Intermediate Similarity	NPC478081
0.7469	Intermediate Similarity	NPC133609
0.7468	Intermediate Similarity	NPC21638
0.7459	Intermediate Similarity	NPC270515
0.7457	Intermediate Similarity	NPC220851
0.7455	Intermediate Similarity	NPC321428
0.7452	Intermediate Similarity	NPC474409
0.7449	Intermediate Similarity	NPC303374
0.7449	Intermediate Similarity	NPC178858
0.7448	Intermediate Similarity	NPC15801
0.7445	Intermediate Similarity	NPC264176
0.7444	Intermediate Similarity	NPC470930
0.7435	Intermediate Similarity	NPC96321
0.743	Intermediate Similarity	NPC160381
0.7429	Intermediate Similarity	NPC165964
0.7426	Intermediate Similarity	NPC475720
0.7426	Intermediate Similarity	NPC474192
0.7421	Intermediate Similarity	NPC315634
0.7421	Intermediate Similarity	NPC100734
0.7421	Intermediate Similarity	NPC88923
0.7418	Intermediate Similarity	NPC17437
0.7409	Intermediate Similarity	NPC306376
0.7401	Intermediate Similarity	NPC220337
0.7397	Intermediate Similarity	NPC478082
0.7397	Intermediate Similarity	NPC477067
0.7397	Intermediate Similarity	NPC473540
0.7362	Intermediate Similarity	NPC227908
0.7361	Intermediate Similarity	NPC246700
0.736	Intermediate Similarity	NPC284685
0.7357	Intermediate Similarity	NPC269367
0.7353	Intermediate Similarity	NPC49547
0.7348	Intermediate Similarity	NPC469928
0.7348	Intermediate Similarity	NPC322064
0.7348	Intermediate Similarity	NPC74969
0.7344	Intermediate Similarity	NPC131486
0.7344	Intermediate Similarity	NPC11408
0.7342	Intermediate Similarity	NPC326363
0.7339	Intermediate Similarity	NPC329982
0.7336	Intermediate Similarity	NPC284141
0.7331	Intermediate Similarity	NPC74575
0.7319	Intermediate Similarity	NPC476818
0.7312	Intermediate Similarity	NPC152620
0.7311	Intermediate Similarity	NPC88363
0.7311	Intermediate Similarity	NPC72980
0.7297	Intermediate Similarity	NPC18487

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 NPC473187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	686
0.2-0.3	979
0.3-0.4	1548
0.4-0.5	2812
0.5-0.6	2027
0.6-0.7	703
0.7-0.8	89
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
0.8009	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7743	Intermediate Similarity	NPD5632	Approved
0.7722	Intermediate Similarity	NPD6790	Phase 1
0.7713	Intermediate Similarity	NPD5416	Discontinued
0.7682	Intermediate Similarity	NPD6962	Phase 2
0.768	Intermediate Similarity	NPD8363	Approved
0.768	Intermediate Similarity	NPD8364	Approved
0.7638	Intermediate Similarity	NPD8428	Approved
0.7638	Intermediate Similarity	NPD8427	Approved
0.7638	Intermediate Similarity	NPD8467	Approved
0.7638	Intermediate Similarity	NPD8465	Approved
0.7638	Intermediate Similarity	NPD8466	Approved
0.7638	Intermediate Similarity	NPD8429	Approved
0.7619	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5488	Discontinued
0.7588	Intermediate Similarity	NPD8459	Approved
0.7588	Intermediate Similarity	NPD8460	Approved
0.7572	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4373	Phase 2
0.7533	Intermediate Similarity	NPD5902	Approved
0.7533	Intermediate Similarity	NPD5903	Approved
0.753	Intermediate Similarity	NPD8091	Phase 3
0.7519	Intermediate Similarity	NPD8426	Approved
0.7519	Intermediate Similarity	NPD8425	Approved
0.75	Intermediate Similarity	NPD5482	Discontinued
0.7489	Intermediate Similarity	NPD4952	Phase 3
0.7489	Intermediate Similarity	NPD3003	Approved
0.7479	Intermediate Similarity	NPD7853	Phase 2
0.7468	Intermediate Similarity	NPD7558	Phase 2
0.7435	Intermediate Similarity	NPD7395	Discontinued
0.7427	Intermediate Similarity	NPD7417	Discontinued
0.7421	Intermediate Similarity	NPD7803	Approved
0.7418	Intermediate Similarity	NPD8358	Approved
0.7404	Intermediate Similarity	NPD3259	Approved
0.7404	Intermediate Similarity	NPD7994	Phase 2
0.7401	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6242	Discontinued
0.7366	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7955	Approved
0.736	Intermediate Similarity	NPD7956	Approved
0.7358	Intermediate Similarity	NPD3986	Discontinued
0.7345	Intermediate Similarity	NPD5658	Approved
0.7345	Intermediate Similarity	NPD2916	Discontinued
0.7342	Intermediate Similarity	NPD5479	Discontinued
0.7304	Intermediate Similarity	NPD5293	Phase 2
0.7285	Intermediate Similarity	NPD5003	Discontinued
0.7265	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6530	Approved
0.7262	Intermediate Similarity	NPD7708	Approved
0.7262	Intermediate Similarity	NPD6531	Approved
0.726	Intermediate Similarity	NPD5937	Approved
0.7257	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7194	Discontinued
0.7241	Intermediate Similarity	NPD7181	Phase 3
0.7234	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6995	Phase 1
0.7225	Intermediate Similarity	NPD5429	Discontinued
0.7225	Intermediate Similarity	NPD7222	Phase 2
0.722	Intermediate Similarity	NPD8396	Approved
0.722	Intermediate Similarity	NPD8395	Approved
0.722	Intermediate Similarity	NPD1768	Approved
0.7212	Intermediate Similarity	NPD8489	Phase 1
0.721	Intermediate Similarity	NPD6985	Discontinued
0.7208	Intermediate Similarity	NPD3746	Discontinued
0.7208	Intermediate Similarity	NPD4885	Approved
0.7173	Intermediate Similarity	NPD3925	Approved
0.7172	Intermediate Similarity	NPD4561	Discontinued
0.7162	Intermediate Similarity	NPD5512	Phase 3
0.7149	Intermediate Similarity	NPD7452	Approved
0.7149	Intermediate Similarity	NPD7453	Approved
0.7148	Intermediate Similarity	NPD5450	Discontinued
0.7143	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5612	Discontinued
0.7117	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6716	Phase 1
0.7107	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD3258	Approved
0.7105	Intermediate Similarity	NPD8403	Phase 1
0.7091	Intermediate Similarity	NPD2565	Phase 2
0.7091	Intermediate Similarity	NPD2564	Approved
0.7082	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7878	Phase 2
0.7064	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD5901	Discontinued
0.7054	Intermediate Similarity	NPD7948	Phase 1
0.7052	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2510	Approved
0.7043	Intermediate Similarity	NPD2509	Approved
0.7037	Intermediate Similarity	NPD6494	Phase 2
0.7037	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8016	Phase 3
0.7031	Intermediate Similarity	NPD5530	Phase 1
0.7021	Intermediate Similarity	NPD5164	Discontinued
0.7	Intermediate Similarity	NPD4948	Discontinued
0.7	Intermediate Similarity	NPD1392	Approved
0.6996	Remote Similarity	NPD7069	Discontinued
0.6996	Remote Similarity	NPD1038	Approved
0.6986	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD648	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3006	Discontinued
0.6979	Remote Similarity	NPD8160	Phase 2
0.6977	Remote Similarity	NPD6456	Discontinued
0.6975	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2792	Approved
0.6964	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7689	Approved
0.6946	Remote Similarity	NPD7221	Approved
0.6946	Remote Similarity	NPD7219	Approved
0.6942	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5399	Discovery
0.6936	Remote Similarity	NPD3257	Approved
0.6929	Remote Similarity	NPD7426	Phase 1
0.6926	Remote Similarity	NPD6228	Discontinued
0.692	Remote Similarity	NPD4429	Discontinued
0.692	Remote Similarity	NPD1926	Approved
0.6914	Remote Similarity	NPD4981	Phase 2
0.6908	Remote Similarity	NPD6517	Phase 3
0.6901	Remote Similarity	NPD4328	Approved
0.6891	Remote Similarity	NPD6974	Phase 3
0.6891	Remote Similarity	NPD3875	Discontinued
0.6889	Remote Similarity	NPD4418	Discontinued
0.6885	Remote Similarity	NPD7688	Phase 1
0.6883	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4502	Phase 2
0.688	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4506	Discontinued
0.6863	Remote Similarity	NPD8463	Approved
0.686	Remote Similarity	NPD3263	Phase 3
0.6856	Remote Similarity	NPD4511	Phase 1
0.6851	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5022	Discontinued
0.6844	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.684	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8102	Discontinued
0.6835	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.683	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.683	Remote Similarity	NPD5913	Phase 3
0.6827	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7671	Approved
0.6824	Remote Similarity	NPD7672	Approved
0.682	Remote Similarity	NPD8284	Discontinued
0.682	Remote Similarity	NPD5519	Discontinued
0.6818	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1505	Phase 2
0.6815	Remote Similarity	NPD5805	Approved
0.6814	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD8524	Approved
0.6809	Remote Similarity	NPD7470	Discontinued
0.6809	Remote Similarity	NPD5066	Phase 2
0.6809	Remote Similarity	NPD5067	Phase 2
0.6803	Remote Similarity	NPD7555	Discontinued
0.6802	Remote Similarity	NPD6964	Approved
0.6802	Remote Similarity	NPD6963	Approved
0.6798	Remote Similarity	NPD7946	Pre-registration
0.6798	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2920	Discontinued
0.6797	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5532	Phase 2
0.6792	Remote Similarity	NPD7180	Phase 3
0.6791	Remote Similarity	NPD1325	Approved
0.6791	Remote Similarity	NPD1326	Approved
0.679	Remote Similarity	NPD7603	Discontinued
0.6787	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7921	Approved
0.6784	Remote Similarity	NPD6550	Discontinued
0.678	Remote Similarity	NPD8097	Phase 3
0.678	Remote Similarity	NPD8096	Phase 3
0.6777	Remote Similarity	NPD7548	Discontinued
0.6776	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD4204	Approved
0.6773	Remote Similarity	NPD4203	Approved
0.6772	Remote Similarity	NPD7658	Phase 2
0.677	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.677	Remote Similarity	NPD802	Phase 2
0.677	Remote Similarity	NPD4539	Phase 1
0.6768	Remote Similarity	NPD7924	Phase 2
0.6768	Remote Similarity	NPD7925	Phase 2
0.6765	Remote Similarity	NPD3393	Approved
0.6765	Remote Similarity	NPD3394	Approved
0.6765	Remote Similarity	NPD3389	Approved
0.6763	Remote Similarity	NPD7556	Discontinued
0.6758	Remote Similarity	NPD7859	Phase 2
0.6754	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6376	Discontinued
0.6751	Remote Similarity	NPD3945	Discontinued
0.6751	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6770	Approved
0.6749	Remote Similarity	NPD2835	Phase 2
0.6747	Remote Similarity	NPD4368	Phase 2
0.6744	Remote Similarity	NPD8244	Phase 2
0.6744	Remote Similarity	NPD2844	Phase 3

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