NPASS Compound

Structure

NPC472111 OpenBabel07101719132D 27 31 0 0 1 0 0 0 0 0999 V2000 -5.3816 0.2456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5535 -0.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2371 0.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0678 -3.4345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1200 -1.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6462 -0.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5948 -2.4941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 0.2262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6768 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 1.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 -1.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -0.2544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5943 -2.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1804 -0.2544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1209 -1.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8506 -1.3764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 0.1310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1804 -1.0253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6466 -0.7628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 -1.5059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8263 0.0547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9253 -0.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6525 -0.5087 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 -4.7140 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0682 -3.4046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -1.0253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 19 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 9 16 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 12 1 1 1 0 0 0 12 17 1 0 0 0 0 12 27 1 0 0 0 0 13 26 1 0 0 0 0 14 8 1 6 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 22 2 0 0 0 0 17 10 1 6 0 0 0 18 11 1 6 0 0 0 18 20 1 0 0 0 0 19 24 1 0 0 0 0 20 9 1 1 0 0 0 20 23 1 0 0 0 0 21 8 1 1 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.23
Volume:	384.104
LogP:	3.262
LogD:	3.084
LogS:	-2.569
# Rotatable Bonds:	2
TPSA:	46.86
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.883
Synthetic Accessibility Score:	5.127
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.293
MDCK Permeability:	1.0661064152373001e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.309
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.85
Plasma Protein Binding (PPB):	69.45429229736328%
Volume Distribution (VD):	1.724
Pgp-substrate:	19.26344108581543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.155
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.588
CYP2D6-inhibitor:	0.757
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.904

ADMET: Excretion

Clearance (CL):	9.469
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.342
Drug-inuced Liver Injury (DILI):	0.697
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.685
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.113
Carcinogencity:	0.554
Eye Corrosion:	0.004
Eye Irritation:	0.032
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC472111

Natural Product ID:	NPC472111
*Common Name:**	GQFQLUZOFRJACZ-SNUJFQBTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GQFQLUZOFRJACZ-SNUJFQBTSA-N
Standard InCHI:	InChI=1S/C22H30N2O3/c1-12-17(10-25)14-8-21-22-16(9-20(23(21)2)18(14)11-27-12)15-7-13(26-4)5-6-19(15)24(22)3/h5-7,12,14,17-18,20-21,25H,8-11H2,1-4H3/t12-,14-,17-,18+,20-,21-/m0/s1
SMILES:	CC1C(C2CC3C4=C(CC(C2CO1)N3C)C5=C(N4C)C=CC(=C5)OC)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338234
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline alkaloids

*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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	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
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[540142]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[540142]

☑ 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 NPC472111 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	420
0.1-0.2	1771
0.2-0.3	9940
0.3-0.4	8031
0.4-0.5	15146
0.5-0.6	4282
0.6-0.7	2511
0.7-0.8	547
0.8-0.85	33
0.85-0.9	15
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8808	High Similarity	NPC47059
0.8808	High Similarity	NPC165349
0.8808	High Similarity	NPC274291
0.8808	High Similarity	NPC264166
0.8808	High Similarity	NPC329708
0.8808	High Similarity	NPC118832
0.8763	High Similarity	NPC475841
0.8763	High Similarity	NPC474145
0.8724	High Similarity	NPC469589
0.8698	High Similarity	NPC249040
0.8687	High Similarity	NPC472098
0.8626	High Similarity	NPC24594
0.8626	High Similarity	NPC472122
0.8571	High Similarity	NPC472099
0.8486	Intermediate Similarity	NPC187827
0.8486	Intermediate Similarity	NPC472105
0.841	Intermediate Similarity	NPC329793
0.8396	Intermediate Similarity	NPC472109
0.8396	Intermediate Similarity	NPC472110
0.8366	Intermediate Similarity	NPC469592
0.8366	Intermediate Similarity	NPC471080
0.8317	Intermediate Similarity	NPC264176
0.8309	Intermediate Similarity	NPC280272
0.83	Intermediate Similarity	NPC475910
0.8293	Intermediate Similarity	NPC469594
0.8201	Intermediate Similarity	NPC472108
0.8201	Intermediate Similarity	NPC139291
0.8182	Intermediate Similarity	NPC326575
0.8112	Intermediate Similarity	NPC251090
0.8103	Intermediate Similarity	NPC279401
0.8103	Intermediate Similarity	NPC79293
0.81	Intermediate Similarity	NPC223427
0.8098	Intermediate Similarity	NPC478074
0.8069	Intermediate Similarity	NPC53344
0.8042	Intermediate Similarity	NPC133261
0.8031	Intermediate Similarity	NPC66083
0.803	Intermediate Similarity	NPC82548
0.801	Intermediate Similarity	NPC307963
0.801	Intermediate Similarity	NPC472104
0.801	Intermediate Similarity	NPC176127
0.8	Intermediate Similarity	NPC474192
0.8	Intermediate Similarity	NPC475720
0.7972	Intermediate Similarity	NPC295228
0.7951	Intermediate Similarity	NPC471304
0.795	Intermediate Similarity	NPC176538
0.7908	Intermediate Similarity	NPC92111
0.7895	Intermediate Similarity	NPC283152
0.7887	Intermediate Similarity	NPC21638
0.7861	Intermediate Similarity	NPC329747
0.786	Intermediate Similarity	NPC253580
0.7857	Intermediate Similarity	NPC76748
0.7854	Intermediate Similarity	NPC470931
0.7847	Intermediate Similarity	NPC152768
0.7847	Intermediate Similarity	NPC148183
0.782	Intermediate Similarity	NPC213530
0.782	Intermediate Similarity	NPC193267
0.7816	Intermediate Similarity	NPC476116
0.7814	Intermediate Similarity	NPC470126
0.7811	Intermediate Similarity	NPC4071
0.7811	Intermediate Similarity	NPC476578
0.7811	Intermediate Similarity	NPC476582
0.7806	Intermediate Similarity	NPC296527
0.7801	Intermediate Similarity	NPC211997
0.7794	Intermediate Similarity	NPC36229
0.7794	Intermediate Similarity	NPC476581
0.7794	Intermediate Similarity	NPC16452
0.7788	Intermediate Similarity	NPC112206
0.7788	Intermediate Similarity	NPC202605
0.7784	Intermediate Similarity	NPC62069
0.7784	Intermediate Similarity	NPC255229
0.7784	Intermediate Similarity	NPC81229
0.7783	Intermediate Similarity	NPC475816
0.7783	Intermediate Similarity	NPC132642
0.7778	Intermediate Similarity	NPC5145
0.7773	Intermediate Similarity	NPC96321
0.7772	Intermediate Similarity	NPC315957
0.7752	Intermediate Similarity	NPC469554
0.7749	Intermediate Similarity	NPC134586
0.7748	Intermediate Similarity	NPC99891
0.7745	Intermediate Similarity	NPC475774
0.7738	Intermediate Similarity	NPC474183
0.7737	Intermediate Similarity	NPC472123
0.7727	Intermediate Similarity	NPC469390
0.7725	Intermediate Similarity	NPC304926
0.7725	Intermediate Similarity	NPC476041
0.772	Intermediate Similarity	NPC15840
0.7718	Intermediate Similarity	NPC313189
0.7717	Intermediate Similarity	NPC473105
0.7707	Intermediate Similarity	NPC475070
0.7705	Intermediate Similarity	NPC26872
0.7703	Intermediate Similarity	NPC26679
0.7703	Intermediate Similarity	NPC53069
0.7703	Intermediate Similarity	NPC296482
0.7703	Intermediate Similarity	NPC202768
0.7696	Intermediate Similarity	NPC295898
0.7692	Intermediate Similarity	NPC123976
0.7692	Intermediate Similarity	NPC167860
0.7685	Intermediate Similarity	NPC11017
0.7677	Intermediate Similarity	NPC469470
0.7677	Intermediate Similarity	NPC469501
0.7676	Intermediate Similarity	NPC26850
0.7672	Intermediate Similarity	NPC317430
0.7667	Intermediate Similarity	NPC151781
0.7667	Intermediate Similarity	NPC316181
0.7667	Intermediate Similarity	NPC74562
0.7664	Intermediate Similarity	NPC310118
0.7656	Intermediate Similarity	NPC150048
0.7656	Intermediate Similarity	NPC288943
0.7656	Intermediate Similarity	NPC203754
0.7656	Intermediate Similarity	NPC208284
0.7653	Intermediate Similarity	NPC472107
0.7653	Intermediate Similarity	NPC79062
0.765	Intermediate Similarity	NPC110151
0.7647	Intermediate Similarity	NPC177404
0.7647	Intermediate Similarity	NPC31930
0.7644	Intermediate Similarity	NPC174672
0.7644	Intermediate Similarity	NPC174758
0.7642	Intermediate Similarity	NPC305984
0.7621	Intermediate Similarity	NPC285558
0.7619	Intermediate Similarity	NPC94157
0.7617	Intermediate Similarity	NPC128115
0.7615	Intermediate Similarity	NPC314954
0.7615	Intermediate Similarity	NPC311906
0.7615	Intermediate Similarity	NPC476997
0.7614	Intermediate Similarity	NPC66210
0.761	Intermediate Similarity	NPC211813
0.7604	Intermediate Similarity	NPC312872
0.7602	Intermediate Similarity	NPC84478
0.7602	Intermediate Similarity	NPC258480
0.7594	Intermediate Similarity	NPC8022
0.7594	Intermediate Similarity	NPC470799
0.7592	Intermediate Similarity	NPC158129
0.7591	Intermediate Similarity	NPC101543
0.7583	Intermediate Similarity	NPC266931
0.758	Intermediate Similarity	NPC476996
0.758	Intermediate Similarity	NPC476998
0.7578	Intermediate Similarity	NPC470784
0.7573	Intermediate Similarity	NPC469440
0.7573	Intermediate Similarity	NPC162484
0.7569	Intermediate Similarity	NPC478078
0.7565	Intermediate Similarity	NPC329982
0.7563	Intermediate Similarity	NPC42591
0.7561	Intermediate Similarity	NPC232727
0.756	Intermediate Similarity	NPC185782
0.7557	Intermediate Similarity	NPC329631
0.755	Intermediate Similarity	NPC472097
0.7549	Intermediate Similarity	NPC287437
0.7548	Intermediate Similarity	NPC135549
0.7548	Intermediate Similarity	NPC193777
0.754	Intermediate Similarity	NPC84508
0.7537	Intermediate Similarity	NPC267928
0.7536	Intermediate Similarity	NPC316981
0.7536	Intermediate Similarity	NPC96405
0.7536	Intermediate Similarity	NPC171409
0.7534	Intermediate Similarity	NPC476994
0.7534	Intermediate Similarity	NPC184680
0.7525	Intermediate Similarity	NPC171171
0.7525	Intermediate Similarity	NPC204385
0.7525	Intermediate Similarity	NPC131017
0.7524	Intermediate Similarity	NPC135887
0.7524	Intermediate Similarity	NPC290689
0.7524	Intermediate Similarity	NPC199277
0.7512	Intermediate Similarity	NPC234197
0.7512	Intermediate Similarity	NPC280964
0.7512	Intermediate Similarity	NPC141915
0.7512	Intermediate Similarity	NPC477019
0.7512	Intermediate Similarity	NPC195268
0.7512	Intermediate Similarity	NPC469928
0.7512	Intermediate Similarity	NPC114335
0.7512	Intermediate Similarity	NPC133140
0.7511	Intermediate Similarity	NPC81175
0.75	Intermediate Similarity	NPC470785
0.75	Intermediate Similarity	NPC476106
0.7489	Intermediate Similarity	NPC473185
0.7488	Intermediate Similarity	NPC473053
0.7488	Intermediate Similarity	NPC476138
0.7488	Intermediate Similarity	NPC245816
0.7488	Intermediate Similarity	NPC245916
0.7487	Intermediate Similarity	NPC472323
0.7477	Intermediate Similarity	NPC96584
0.7477	Intermediate Similarity	NPC255800
0.7475	Intermediate Similarity	NPC62510
0.7475	Intermediate Similarity	NPC314002
0.7475	Intermediate Similarity	NPC289786
0.7466	Intermediate Similarity	NPC201508
0.7464	Intermediate Similarity	NPC193238
0.7463	Intermediate Similarity	NPC128823
0.7457	Intermediate Similarity	NPC478080
0.7453	Intermediate Similarity	NPC203168
0.7453	Intermediate Similarity	NPC48353
0.7452	Intermediate Similarity	NPC164374
0.7452	Intermediate Similarity	NPC137929
0.7451	Intermediate Similarity	NPC70956
0.7451	Intermediate Similarity	NPC224928
0.7451	Intermediate Similarity	NPC243834
0.7442	Intermediate Similarity	NPC303658
0.7441	Intermediate Similarity	NPC219664
0.7437	Intermediate Similarity	NPC61350
0.743	Intermediate Similarity	NPC274982
0.7429	Intermediate Similarity	NPC287208

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 NPC472111 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	584
0.2-0.3	768
0.3-0.4	1196
0.4-0.5	2474
0.5-0.6	2551
0.6-0.7	1100
0.7-0.8	235
0.8-0.85	12
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8808	High Similarity	NPD4033	Approved
0.8808	High Similarity	NPD4035	Approved
0.8808	High Similarity	NPD4036	Approved
0.8808	High Similarity	NPD4037	Approved
0.8808	High Similarity	NPD32	Approved
0.8808	High Similarity	NPD4034	Approved
0.8808	High Similarity	NPD4039	Approved
0.8808	High Similarity	NPD4122	Approved
0.8808	High Similarity	NPD31	Approved
0.8808	High Similarity	NPD4038	Approved
0.8622	High Similarity	NPD7222	Phase 2
0.8342	Intermediate Similarity	NPD7453	Approved
0.8342	Intermediate Similarity	NPD7452	Approved
0.8342	Intermediate Similarity	NPD4203	Approved
0.8342	Intermediate Similarity	NPD4204	Approved
0.8265	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD4418	Discontinued
0.8119	Intermediate Similarity	NPD5658	Approved
0.8109	Intermediate Similarity	NPD5530	Phase 1
0.8021	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD1038	Approved
0.797	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7797	Approved
0.7917	Intermediate Similarity	NPD7796	Approved
0.7882	Intermediate Similarity	NPD4795	Phase 2
0.7868	Intermediate Similarity	NPD6569	Phase 2
0.7843	Intermediate Similarity	NPD3003	Approved
0.7839	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7839	Intermediate Similarity	NPD3477	Phase 2
0.7828	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD7194	Discontinued
0.78	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD1739	Approved
0.7772	Intermediate Similarity	NPD1740	Approved
0.7762	Intermediate Similarity	NPD7112	Discontinued
0.7755	Intermediate Similarity	NPD2383	Phase 1
0.774	Intermediate Similarity	NPD4502	Phase 2
0.7723	Intermediate Similarity	NPD1768	Approved
0.7714	Intermediate Similarity	NPD4897	Phase 2
0.771	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD3816	Phase 1
0.7703	Intermediate Similarity	NPD3815	Phase 1
0.7703	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5930	Phase 3
0.7685	Intermediate Similarity	NPD7674	Phase 3
0.7685	Intermediate Similarity	NPD7675	Phase 3
0.7685	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7678	Intermediate Similarity	NPD5612	Discontinued
0.7661	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD6991	Approved
0.7642	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD5256	Discontinued
0.7604	Intermediate Similarity	NPD7426	Phase 1
0.7598	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6276	Discontinued
0.7577	Intermediate Similarity	NPD3920	Phase 2
0.7576	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1034	Phase 3
0.757	Intermediate Similarity	NPD3875	Discontinued
0.7562	Intermediate Similarity	NPD4551	Phase 2
0.7561	Intermediate Similarity	NPD6592	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6494	Phase 2
0.7557	Intermediate Similarity	NPD7558	Phase 2
0.7548	Intermediate Similarity	NPD1392	Approved
0.7547	Intermediate Similarity	NPD5903	Approved
0.7547	Intermediate Similarity	NPD5902	Approved
0.7546	Intermediate Similarity	NPD7221	Approved
0.7546	Intermediate Similarity	NPD7219	Approved
0.7545	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD8016	Phase 3
0.7534	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD6590	Discontinued
0.7523	Intermediate Similarity	NPD6985	Discontinued
0.7512	Intermediate Similarity	NPD3921	Approved
0.7512	Intermediate Similarity	NPD7671	Approved
0.7512	Intermediate Similarity	NPD3923	Approved
0.7512	Intermediate Similarity	NPD7672	Approved
0.7512	Intermediate Similarity	NPD3922	Approved
0.7512	Intermediate Similarity	NPD3924	Approved
0.7512	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5506	Approved
0.75	Intermediate Similarity	NPD3037	Phase 1
0.75	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5507	Approved
0.75	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD6550	Discontinued
0.7477	Intermediate Similarity	NPD6246	Approved
0.7475	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD2177	Approved
0.7463	Intermediate Similarity	NPD2176	Approved
0.7463	Intermediate Similarity	NPD2175	Phase 3
0.7455	Intermediate Similarity	NPD5559	Phase 2
0.744	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6159	Phase 2
0.7435	Intermediate Similarity	NPD8101	Phase 3
0.7432	Intermediate Similarity	NPD4885	Approved
0.7422	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8463	Approved
0.7411	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD6220	Phase 3
0.7403	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD5512	Phase 3
0.7396	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5293	Phase 2
0.738	Intermediate Similarity	NPD8359	Phase 2
0.7379	Intermediate Similarity	NPD3825	Phase 3
0.7373	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7069	Discontinued
0.7362	Intermediate Similarity	NPD7955	Approved
0.7362	Intermediate Similarity	NPD7956	Approved
0.7361	Intermediate Similarity	NPD3354	Phase 2
0.7358	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1032	Phase 2
0.7346	Intermediate Similarity	NPD2187	Approved
0.7346	Intermediate Similarity	NPD2189	Approved
0.7343	Intermediate Similarity	NPD4501	Approved
0.7343	Intermediate Similarity	NPD4500	Approved
0.7336	Intermediate Similarity	NPD5945	Phase 1
0.7336	Intermediate Similarity	NPD5944	Phase 1
0.7336	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD3402	Phase 1
0.7327	Intermediate Similarity	NPD6281	Approved
0.7327	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5067	Phase 2
0.7324	Intermediate Similarity	NPD3570	Phase 2
0.7324	Intermediate Similarity	NPD5066	Phase 2
0.7318	Intermediate Similarity	NPD7719	Discontinued
0.7313	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD1856	Discontinued
0.7304	Intermediate Similarity	NPD8100	Phase 3
0.7304	Intermediate Similarity	NPD6361	Phase 2
0.73	Intermediate Similarity	NPD6227	Discontinued
0.7299	Intermediate Similarity	NPD5429	Discontinued
0.7297	Intermediate Similarity	NPD7555	Discontinued
0.7295	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6856	Discontinued
0.7294	Intermediate Similarity	NPD6242	Discontinued
0.7293	Intermediate Similarity	NPD6572	Phase 2
0.7293	Intermediate Similarity	NPD6573	Phase 3
0.7286	Intermediate Similarity	NPD3397	Phase 2
0.7282	Intermediate Similarity	NPD2952	Discontinued
0.7281	Intermediate Similarity	NPD6568	Discontinued
0.7281	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7417	Discontinued
0.7277	Intermediate Similarity	NPD4021	Phase 2
0.7273	Intermediate Similarity	NPD2882	Phase 1
0.7273	Intermediate Similarity	NPD8358	Approved
0.7273	Intermediate Similarity	NPD6158	Phase 2
0.7273	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3396	Approved
0.7268	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3395	Approved
0.7265	Intermediate Similarity	NPD7567	Approved
0.7264	Intermediate Similarity	NPD2916	Discontinued
0.7264	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4375	Approved
0.726	Intermediate Similarity	NPD4600	Approved
0.726	Intermediate Similarity	NPD4601	Approved
0.7257	Intermediate Similarity	NPD7708	Approved
0.7252	Intermediate Similarity	NPD6327	Phase 1
0.7252	Intermediate Similarity	NPD6326	Phase 2
0.7251	Intermediate Similarity	NPD5601	Phase 2
0.7248	Intermediate Similarity	NPD3258	Approved
0.7243	Intermediate Similarity	NPD5939	Approved
0.7243	Intermediate Similarity	NPD5936	Approved
0.7241	Intermediate Similarity	NPD8063	Discontinued
0.7241	Intermediate Similarity	NPD8102	Discontinued
0.7236	Intermediate Similarity	NPD3386	Phase 2
0.723	Intermediate Similarity	NPD4437	Phase 3
0.7228	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6290	Phase 2
0.7214	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4889	Approved
0.7211	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.721	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5097	Phase 2
0.7208	Intermediate Similarity	NPD2380	Approved
0.7208	Intermediate Similarity	NPD2382	Approved
0.7208	Intermediate Similarity	NPD7803	Approved
0.7208	Intermediate Similarity	NPD2381	Approved
0.7206	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5913	Phase 3
0.7198	Intermediate Similarity	NPD1622	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