NPASS Compound

Structure

NPC475778 OpenBabel07101718312D 25 29 0 0 1 0 0 0 0 0999 V2000 2.2569 2.7999 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 -1.9890 -1.8271 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 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1142 -0.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1100 -1.5161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4197 -1.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1100 -0.1019 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 -1.8090 0.0000 C 0 0 2 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 2.6831 -0.3090 0.0000 C 0 0 2 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 2.2969 1.0683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0566 -1.1020 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 3.2967 1.0915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1118 -2.2125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7770 1.9226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8171 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 11 2 0 0 0 0 5 13 2 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 8 25 1 0 0 0 0 9 19 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 6 0 0 0 13 21 1 0 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 17 1 6 0 0 0 19 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.16
Volume:	338.37
LogP:	1.285
LogD:	1.258
LogS:	-3.2
# Rotatable Bonds:	2
TPSA:	83.58
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	5.137
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.773
MDCK Permeability:	8.202624485420529e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	33.32077407836914%
Volume Distribution (VD):	1.692
Pgp-substrate:	65.19683837890625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.218
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.446
CYP3A4-inhibitor:	0.279
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	3.609
Half-life (T1/2):	0.451

ADMET: Toxicity

hERG Blockers:	0.824
Human Hepatotoxicity (H-HT):	0.405
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.836
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.398
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC475778

Natural Product ID:	NPC475778
*Common Name:**	Alstilobanine E
IUPAC Name:	n.a.
Synonyms:	Alstilobanine E
Standard InCHIKey:	DOXPGQDQGREMMW-NCGUTPBLSA-N
Standard InCHI:	InChI=1S/C19H22N2O4/c1-24-17(22)18-10-25-8-12(19(23)9-20-7-6-14(18)19)15-11-4-2-3-5-13(11)21-16(15)18/h2-5,12,14,20-21,23H,6-10H2,1H3/t12-,14-,18-,19-/m1/s1
SMILES:	COC(=O)[C@@]12COC[C@H](c3c1[nH]c1c3cccc1)[C@]1([C@@H]2CCNC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515232
PubChem CID:	44561425
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
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	6.8	%	PMID[538022]

☑ 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 NPC475778 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	281
0.1-0.2	1432
0.2-0.3	5403
0.3-0.4	21933
0.4-0.5	8597
0.5-0.6	2687
0.6-0.7	1895
0.7-0.8	434
0.8-0.85	27
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9788	High Similarity	NPC234999
0.9115	High Similarity	NPC474116
0.9016	High Similarity	NPC162730
0.8814	High Similarity	NPC214428
0.8593	High Similarity	NPC277350
0.8542	High Similarity	NPC329858
0.8465	Intermediate Similarity	NPC469743
0.8454	Intermediate Similarity	NPC55493
0.8384	Intermediate Similarity	NPC241024
0.8358	Intermediate Similarity	NPC475847
0.8358	Intermediate Similarity	NPC185742
0.8351	Intermediate Similarity	NPC314333
0.8342	Intermediate Similarity	NPC313985
0.8342	Intermediate Similarity	NPC49196
0.8342	Intermediate Similarity	NPC79129
0.8342	Intermediate Similarity	NPC249150
0.8342	Intermediate Similarity	NPC81654
0.8342	Intermediate Similarity	NPC195461
0.8309	Intermediate Similarity	NPC469928
0.8241	Intermediate Similarity	NPC50503
0.8241	Intermediate Similarity	NPC52557
0.8112	Intermediate Similarity	NPC175474
0.8048	Intermediate Similarity	NPC330009
0.8041	Intermediate Similarity	NPC19679
0.8	Intermediate Similarity	NPC85066
0.8	Intermediate Similarity	NPC181502
0.7972	Intermediate Similarity	NPC96321
0.7945	Intermediate Similarity	NPC475720
0.7945	Intermediate Similarity	NPC474192
0.791	Intermediate Similarity	NPC474121
0.7887	Intermediate Similarity	NPC219336
0.7874	Intermediate Similarity	NPC18661
0.7846	Intermediate Similarity	NPC469896
0.7835	Intermediate Similarity	NPC183662
0.7835	Intermediate Similarity	NPC15573
0.7835	Intermediate Similarity	NPC217372
0.7834	Intermediate Similarity	NPC235885
0.7795	Intermediate Similarity	NPC213468
0.7783	Intermediate Similarity	NPC472291
0.7783	Intermediate Similarity	NPC229348
0.7739	Intermediate Similarity	NPC99428
0.7739	Intermediate Similarity	NPC235684
0.7733	Intermediate Similarity	NPC475816
0.7732	Intermediate Similarity	NPC329688
0.7732	Intermediate Similarity	NPC189812
0.7729	Intermediate Similarity	NPC476874
0.7721	Intermediate Similarity	NPC473041
0.7716	Intermediate Similarity	NPC478080
0.7711	Intermediate Similarity	NPC95783
0.771	Intermediate Similarity	NPC204491
0.771	Intermediate Similarity	NPC203614
0.7706	Intermediate Similarity	NPC266192
0.7696	Intermediate Similarity	NPC2395
0.7692	Intermediate Similarity	NPC477135
0.7668	Intermediate Similarity	NPC70155
0.7667	Intermediate Similarity	NPC477065
0.7647	Intermediate Similarity	NPC311906
0.7644	Intermediate Similarity	NPC193761
0.7639	Intermediate Similarity	NPC281049
0.7636	Intermediate Similarity	NPC267926
0.7636	Intermediate Similarity	NPC112547
0.7612	Intermediate Similarity	NPC472323
0.7608	Intermediate Similarity	NPC476098
0.7602	Intermediate Similarity	NPC57690
0.7598	Intermediate Similarity	NPC472210
0.7598	Intermediate Similarity	NPC247735
0.7598	Intermediate Similarity	NPC472295
0.7598	Intermediate Similarity	NPC269886
0.7598	Intermediate Similarity	NPC81802
0.7589	Intermediate Similarity	NPC473105
0.7588	Intermediate Similarity	NPC473540
0.7581	Intermediate Similarity	NPC478157
0.7581	Intermediate Similarity	NPC474412
0.7574	Intermediate Similarity	NPC111602
0.7574	Intermediate Similarity	NPC102338
0.7574	Intermediate Similarity	NPC196251
0.7574	Intermediate Similarity	NPC63199
0.757	Intermediate Similarity	NPC151976
0.757	Intermediate Similarity	NPC87856
0.7563	Intermediate Similarity	NPC111275
0.7562	Intermediate Similarity	NPC315555
0.756	Intermediate Similarity	NPC137589
0.7559	Intermediate Similarity	NPC471304
0.755	Intermediate Similarity	NPC472119
0.7549	Intermediate Similarity	NPC472113
0.7546	Intermediate Similarity	NPC132211
0.7545	Intermediate Similarity	NPC475271
0.7538	Intermediate Similarity	NPC71037
0.7537	Intermediate Similarity	NPC472112
0.7535	Intermediate Similarity	NPC267965
0.7526	Intermediate Similarity	NPC154293
0.7525	Intermediate Similarity	NPC248041
0.7525	Intermediate Similarity	NPC283219
0.7525	Intermediate Similarity	NPC126709
0.7524	Intermediate Similarity	NPC231342
0.7524	Intermediate Similarity	NPC205403
0.7513	Intermediate Similarity	NPC267885
0.7512	Intermediate Similarity	NPC478158
0.7512	Intermediate Similarity	NPC476319
0.7511	Intermediate Similarity	NPC141428
0.75	Intermediate Similarity	NPC472108
0.75	Intermediate Similarity	NPC290529
0.75	Intermediate Similarity	NPC139291
0.7477	Intermediate Similarity	NPC475424
0.7477	Intermediate Similarity	NPC472762
0.7477	Intermediate Similarity	NPC82070
0.7477	Intermediate Similarity	NPC79107
0.7476	Intermediate Similarity	NPC276517
0.7466	Intermediate Similarity	NPC64216
0.7466	Intermediate Similarity	NPC147446
0.7465	Intermediate Similarity	NPC476114
0.7462	Intermediate Similarity	NPC472586
0.7462	Intermediate Similarity	NPC203468
0.7462	Intermediate Similarity	NPC149155
0.7462	Intermediate Similarity	NPC110500
0.7457	Intermediate Similarity	NPC17437
0.7442	Intermediate Similarity	NPC204303
0.744	Intermediate Similarity	NPC245916
0.744	Intermediate Similarity	NPC11445
0.7438	Intermediate Similarity	NPC119700
0.7437	Intermediate Similarity	NPC472443
0.7436	Intermediate Similarity	NPC78020
0.7436	Intermediate Similarity	NPC317430
0.7431	Intermediate Similarity	NPC312645
0.743	Intermediate Similarity	NPC271862
0.7422	Intermediate Similarity	NPC474877
0.7419	Intermediate Similarity	NPC313640
0.7416	Intermediate Similarity	NPC32200
0.7413	Intermediate Similarity	NPC472444
0.7411	Intermediate Similarity	NPC33949
0.7409	Intermediate Similarity	NPC16667
0.7402	Intermediate Similarity	NPC321708
0.74	Intermediate Similarity	NPC300688
0.74	Intermediate Similarity	NPC15840
0.7398	Intermediate Similarity	NPC280548
0.7398	Intermediate Similarity	NPC195788
0.7398	Intermediate Similarity	NPC237901
0.7393	Intermediate Similarity	NPC476073
0.7391	Intermediate Similarity	NPC220151
0.7391	Intermediate Similarity	NPC57994
0.7391	Intermediate Similarity	NPC195239
0.7391	Intermediate Similarity	NPC19692
0.7391	Intermediate Similarity	NPC289299
0.7391	Intermediate Similarity	NPC157828
0.7387	Intermediate Similarity	NPC14113
0.7387	Intermediate Similarity	NPC145885
0.7387	Intermediate Similarity	NPC151939
0.7387	Intermediate Similarity	NPC84827
0.7385	Intermediate Similarity	NPC74969
0.7385	Intermediate Similarity	NPC251936
0.7383	Intermediate Similarity	NPC258062
0.7383	Intermediate Similarity	NPC127677
0.7382	Intermediate Similarity	NPC285469
0.7381	Intermediate Similarity	NPC312870
0.7381	Intermediate Similarity	NPC294909
0.7381	Intermediate Similarity	NPC199851
0.7381	Intermediate Similarity	NPC254240
0.7381	Intermediate Similarity	NPC128265
0.7378	Intermediate Similarity	NPC470729
0.7378	Intermediate Similarity	NPC477176
0.7376	Intermediate Similarity	NPC165201
0.7366	Intermediate Similarity	NPC206967
0.7364	Intermediate Similarity	NPC52254
0.7363	Intermediate Similarity	NPC302191
0.736	Intermediate Similarity	NPC6982
0.7359	Intermediate Similarity	NPC478081
0.7358	Intermediate Similarity	NPC165599
0.7358	Intermediate Similarity	NPC98715
0.7354	Intermediate Similarity	NPC476818
0.735	Intermediate Similarity	NPC55772
0.735	Intermediate Similarity	NPC270009
0.7349	Intermediate Similarity	NPC284102
0.734	Intermediate Similarity	NPC472107
0.734	Intermediate Similarity	NPC79062
0.7336	Intermediate Similarity	NPC225821
0.7336	Intermediate Similarity	NPC46225
0.7336	Intermediate Similarity	NPC244741
0.7333	Intermediate Similarity	NPC470508
0.733	Intermediate Similarity	NPC472097
0.7327	Intermediate Similarity	NPC75634
0.7327	Intermediate Similarity	NPC472110
0.7327	Intermediate Similarity	NPC477159
0.7327	Intermediate Similarity	NPC472109
0.7327	Intermediate Similarity	NPC469358
0.7325	Intermediate Similarity	NPC94428
0.7325	Intermediate Similarity	NPC263937
0.7324	Intermediate Similarity	NPC314648
0.7323	Intermediate Similarity	NPC34508
0.7323	Intermediate Similarity	NPC472123
0.7321	Intermediate Similarity	NPC90967
0.7321	Intermediate Similarity	NPC319232
0.7321	Intermediate Similarity	NPC24370
0.7317	Intermediate Similarity	NPC46413
0.7316	Intermediate Similarity	NPC477066
0.7315	Intermediate Similarity	NPC475165
0.7311	Intermediate Similarity	NPC260900
0.7306	Intermediate Similarity	NPC152768
0.7306	Intermediate Similarity	NPC148183
0.7304	Intermediate Similarity	NPC160381
0.7304	Intermediate Similarity	NPC62749

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 NPC475778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	488
0.2-0.3	637
0.3-0.4	1803
0.4-0.5	2962
0.5-0.6	2366
0.6-0.7	645
0.7-0.8	75
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8351	Intermediate Similarity	NPD4499	Approved
0.8342	Intermediate Similarity	NPD4600	Approved
0.8342	Intermediate Similarity	NPD4601	Approved
0.8191	Intermediate Similarity	NPD5003	Discontinued
0.794	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD2565	Phase 2
0.7889	Intermediate Similarity	NPD2564	Approved
0.7778	Intermediate Similarity	NPD2920	Discontinued
0.7729	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD2095	Phase 2
0.7588	Intermediate Similarity	NPD2094	Phase 2
0.7588	Intermediate Similarity	NPD2092	Phase 2
0.7588	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2096	Phase 2
0.755	Intermediate Similarity	NPD2091	Phase 2
0.7536	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7957	Phase 1
0.7513	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD5426	Phase 3
0.7462	Intermediate Similarity	NPD482	Approved
0.7457	Intermediate Similarity	NPD8358	Approved
0.7453	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7470	Discontinued
0.7441	Intermediate Similarity	NPD8072	Approved
0.7441	Intermediate Similarity	NPD6176	Phase 1
0.7436	Intermediate Similarity	NPD2844	Phase 3
0.7406	Intermediate Similarity	NPD5901	Discontinued
0.7398	Intermediate Similarity	NPD8467	Approved
0.7398	Intermediate Similarity	NPD8466	Approved
0.7398	Intermediate Similarity	NPD8465	Approved
0.7393	Intermediate Similarity	NPD8073	Approved
0.7391	Intermediate Similarity	NPD4602	Approved
0.7381	Intermediate Similarity	NPD4500	Approved
0.7381	Intermediate Similarity	NPD4501	Approved
0.7366	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8363	Approved
0.7366	Intermediate Similarity	NPD8364	Approved
0.7364	Intermediate Similarity	NPD6770	Approved
0.7358	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5913	Phase 3
0.733	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7234	Approved
0.7317	Intermediate Similarity	NPD1534	Approved
0.7317	Intermediate Similarity	NPD7233	Approved
0.7315	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1325	Approved
0.731	Intermediate Similarity	NPD1326	Approved
0.7306	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2916	Discontinued
0.7301	Intermediate Similarity	NPD7824	Approved
0.7286	Intermediate Similarity	NPD7778	Approved
0.7286	Intermediate Similarity	NPD7777	Approved
0.7286	Intermediate Similarity	NPD53	Approved
0.728	Intermediate Similarity	NPD8425	Approved
0.728	Intermediate Similarity	NPD8459	Approved
0.728	Intermediate Similarity	NPD8460	Approved
0.728	Intermediate Similarity	NPD8426	Approved
0.7258	Intermediate Similarity	NPD8428	Approved
0.7258	Intermediate Similarity	NPD8427	Approved
0.7258	Intermediate Similarity	NPD8429	Approved
0.7251	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD750	Phase 2
0.7233	Intermediate Similarity	NPD4334	Discontinued
0.7222	Intermediate Similarity	NPD2510	Approved
0.7222	Intermediate Similarity	NPD2509	Approved
0.7217	Intermediate Similarity	NPD484	Approved
0.7212	Intermediate Similarity	NPD7731	Approved
0.7212	Intermediate Similarity	NPD7730	Approved
0.7205	Intermediate Similarity	NPD7951	Approved
0.7205	Intermediate Similarity	NPD7790	Approved
0.7205	Intermediate Similarity	NPD7791	Approved
0.7205	Intermediate Similarity	NPD7950	Approved
0.7205	Intermediate Similarity	NPD7953	Approved
0.7205	Intermediate Similarity	NPD7952	Approved
0.7205	Intermediate Similarity	NPD7789	Approved
0.7204	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7271	Approved
0.7184	Intermediate Similarity	NPD4948	Discontinued
0.7178	Intermediate Similarity	NPD4076	Approved
0.7178	Intermediate Similarity	NPD4079	Approved
0.717	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6987	Phase 1
0.7162	Intermediate Similarity	NPD7878	Phase 2
0.7149	Intermediate Similarity	NPD3393	Approved
0.7149	Intermediate Similarity	NPD3394	Approved
0.7149	Intermediate Similarity	NPD3389	Approved
0.7149	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5891	Approved
0.7143	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4427	Phase 2
0.7136	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3506	Approved
0.7129	Intermediate Similarity	NPD3505	Approved
0.7123	Intermediate Similarity	NPD4397	Phase 1
0.7118	Intermediate Similarity	NPD7688	Phase 1
0.7117	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6995	Phase 1
0.711	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4506	Discontinued
0.7094	Intermediate Similarity	NPD8386	Phase 2
0.7091	Intermediate Similarity	NPD7454	Approved
0.7091	Intermediate Similarity	NPD7455	Approved
0.7089	Intermediate Similarity	NPD6248	Phase 2
0.7089	Intermediate Similarity	NPD6249	Phase 2
0.7085	Intermediate Similarity	NPD5632	Approved
0.7083	Intermediate Similarity	NPD8098	Approved
0.7078	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6664	Approved
0.7073	Intermediate Similarity	NPD5596	Phase 2
0.7064	Intermediate Similarity	NPD6376	Discontinued
0.7059	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4315	Phase 2
0.7043	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7955	Approved
0.7037	Intermediate Similarity	NPD7956	Approved
0.7031	Intermediate Similarity	NPD7780	Approved
0.7031	Intermediate Similarity	NPD7781	Approved
0.7028	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7727	Phase 2
0.7019	Intermediate Similarity	NPD8431	Approved
0.7018	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8093	Discontinued
0.7008	Intermediate Similarity	NPD7708	Approved
0.7005	Intermediate Similarity	NPD8114	Approved
0.7005	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8115	Approved
0.7	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5021	Discontinued
0.7	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7770	Phase 3
0.6987	Remote Similarity	NPD6978	Phase 2
0.6987	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7618	Phase 3
0.6981	Remote Similarity	NPD7619	Phase 3
0.698	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5897	Approved
0.6976	Remote Similarity	NPD5899	Approved
0.6976	Remote Similarity	NPD5898	Approved
0.6974	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD8489	Phase 1
0.6972	Remote Similarity	NPD7001	Phase 3
0.6968	Remote Similarity	NPD5475	Discontinued
0.6964	Remote Similarity	NPD7803	Approved
0.696	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5487	Phase 1
0.6958	Remote Similarity	NPD5482	Discontinued
0.6958	Remote Similarity	NPD7769	Phase 3
0.6955	Remote Similarity	NPD4520	Approved
0.695	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7716	Approved
0.693	Remote Similarity	NPD7717	Approved
0.6927	Remote Similarity	NPD8282	Approved
0.6927	Remote Similarity	NPD7103	Approved
0.6927	Remote Similarity	NPD8283	Approved
0.6927	Remote Similarity	NPD56	Approved
0.6916	Remote Similarity	NPD5506	Approved
0.6916	Remote Similarity	NPD5507	Approved
0.6912	Remote Similarity	NPD2382	Approved
0.6912	Remote Similarity	NPD2380	Approved
0.6912	Remote Similarity	NPD2381	Approved
0.6909	Remote Similarity	NPD8399	Phase 1
0.6909	Remote Similarity	NPD8423	Phase 2
0.6908	Remote Similarity	NPD3320	Approved
0.6908	Remote Similarity	NPD3318	Approved
0.6908	Remote Similarity	NPD3319	Phase 1
0.6906	Remote Similarity	NPD3794	Approved
0.6906	Remote Similarity	NPD8094	Discontinued
0.6906	Remote Similarity	NPD3795	Approved
0.6905	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6455	Phase 3
0.6901	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6479	Discontinued
0.6898	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6182	Approved
0.6897	Remote Similarity	NPD43	Approved
0.6897	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3003	Approved
0.6895	Remote Similarity	NPD7010	Phase 3
0.6893	Remote Similarity	NPD5473	Discontinued
0.6893	Remote Similarity	NPD6452	Discontinued
0.6893	Remote Similarity	NPD6595	Phase 3
0.6889	Remote Similarity	NPD8325	Phase 3
0.6889	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8326	Phase 3
0.6878	Remote Similarity	NPD5834	Phase 3
0.6878	Remote Similarity	NPD5835	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