NPASS Compound

Structure

NPC472104 OpenBabel07101718242D 27 32 0 0 1 0 0 0 0 0999 V2000 1.3084 0.7440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -2.3235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8818 1.2136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9338 -2.2413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4999 -1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9759 -2.1406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1082 -0.5822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1247 0.7004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8341 -1.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7747 -0.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7917 -0.0688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8370 -2.7152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5842 -1.2608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4888 0.2822 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6682 -0.9631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5442 -0.4582 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1503 -0.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9631 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8341 0.4816 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5613 -0.0590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6682 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2592 -0.2334 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5842 0.2976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.7364 -3.6731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8984 -0.2733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 -2.1491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 12 1 0 0 0 0 3 23 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 13 2 0 0 0 0 7 17 2 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 18 1 0 0 0 0 10 26 1 0 0 0 0 11 1 1 6 0 0 0 11 20 1 0 0 0 0 11 26 1 0 0 0 0 12 25 2 0 0 0 0 12 27 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 8 1 1 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 10 1 1 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 1 0 0 0 19 21 1 0 0 0 0 19 24 1 1 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.19
Volume:	372.911
LogP:	3.289
LogD:	3.291
LogS:	-4.46
# Rotatable Bonds:	2
TPSA:	43.7
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	5.972
Fsp3:	0.591
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:	-5.039
MDCK Permeability:	4.625048677553423e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.97
Human Intestinal Absorption (HIA):	0.369
20% Bioavailability (F20%):	0.862
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.321
Plasma Protein Binding (PPB):	69.5488052368164%
Volume Distribution (VD):	2.444
Pgp-substrate:	28.758317947387695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.205
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.48
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.473
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.177
CYP3A4-substrate:	0.754

ADMET: Excretion

Clearance (CL):	5.4
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.876
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.506
Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.095
Carcinogencity:	0.692
Eye Corrosion:	0.005
Eye Irritation:	0.022
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: NPC472104

Natural Product ID:	NPC472104
*Common Name:**	NIVGFWXFJATDQP-GZDNATGCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NIVGFWXFJATDQP-GZDNATGCSA-N
Standard InCHI:	InChI=1S/C22H26N2O3/c1-11-20-14-8-19-21-15(13-6-4-5-7-17(13)23(21)3)9-18(16(14)10-26-11)24(19)22(20)27-12(2)25/h4-7,11,14,16,18-20,22H,8-10H2,1-3H3/t11-,14+,16+,18-,19-,20-,22+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@H]2[C@H](C)OC[C@@H]3[C@H]2C[C@@H]2N1[C@H]3Cc1c2n(C)c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338227
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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

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[514737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[514737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40000.0	nM	PMID[514737]

☑ 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 NPC472104 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	288
0.1-0.2	1533
0.2-0.3	8081
0.3-0.4	23269
0.4-0.5	4931
0.5-0.6	2580
0.6-0.7	1746
0.7-0.8	239
0.8-0.85	20
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC472105
0.9398	High Similarity	NPC187827
0.9217	High Similarity	NPC472122
0.9217	High Similarity	NPC24594
0.8947	High Similarity	NPC472109
0.8947	High Similarity	NPC472110
0.8914	High Similarity	NPC472097
0.8736	High Similarity	NPC472107
0.8736	High Similarity	NPC79062
0.8728	High Similarity	NPC139291
0.8728	High Similarity	NPC472108
0.8727	High Similarity	NPC81229
0.8727	High Similarity	NPC255229
0.8678	High Similarity	NPC472119
0.8621	High Similarity	NPC143533
0.8605	High Similarity	NPC326575
0.8555	High Similarity	NPC133261
0.8539	High Similarity	NPC469501
0.8539	High Similarity	NPC469470
0.8475	Intermediate Similarity	NPC66210
0.8466	Intermediate Similarity	NPC258480
0.8427	Intermediate Similarity	NPC472323
0.8407	Intermediate Similarity	NPC245916
0.84	Intermediate Similarity	NPC15840
0.8324	Intermediate Similarity	NPC472123
0.8216	Intermediate Similarity	NPC52557
0.8207	Intermediate Similarity	NPC472116
0.8128	Intermediate Similarity	NPC254240
0.8128	Intermediate Similarity	NPC128265
0.8128	Intermediate Similarity	NPC199851
0.8128	Intermediate Similarity	NPC312870
0.8128	Intermediate Similarity	NPC294909
0.8077	Intermediate Similarity	NPC175474
0.8054	Intermediate Similarity	NPC289299
0.8054	Intermediate Similarity	NPC57994
0.8043	Intermediate Similarity	NPC472113
0.8033	Intermediate Similarity	NPC472112
0.8032	Intermediate Similarity	NPC249150
0.8032	Intermediate Similarity	NPC81654
0.8032	Intermediate Similarity	NPC79129
0.8032	Intermediate Similarity	NPC49196
0.8032	Intermediate Similarity	NPC195461
0.8032	Intermediate Similarity	NPC313985
0.801	Intermediate Similarity	NPC238457
0.801	Intermediate Similarity	NPC472111
0.7978	Intermediate Similarity	NPC234987
0.7978	Intermediate Similarity	NPC111602
0.7978	Intermediate Similarity	NPC102338
0.7978	Intermediate Similarity	NPC196251
0.7978	Intermediate Similarity	NPC63199
0.7967	Intermediate Similarity	NPC478077
0.7926	Intermediate Similarity	NPC50503
0.7874	Intermediate Similarity	NPC469541
0.7841	Intermediate Similarity	NPC317430
0.7747	Intermediate Similarity	NPC113626
0.7727	Intermediate Similarity	NPC234078
0.7727	Intermediate Similarity	NPC221100
0.7725	Intermediate Similarity	NPC20144
0.7717	Intermediate Similarity	NPC62510
0.7714	Intermediate Similarity	NPC194881
0.7711	Intermediate Similarity	NPC52254
0.7692	Intermediate Similarity	NPC469896
0.768	Intermediate Similarity	NPC14325
0.768	Intermediate Similarity	NPC28848
0.7677	Intermediate Similarity	NPC472098
0.7667	Intermediate Similarity	NPC189812
0.7667	Intermediate Similarity	NPC329688
0.7654	Intermediate Similarity	NPC126492
0.7641	Intermediate Similarity	NPC475841
0.7641	Intermediate Similarity	NPC474145
0.7586	Intermediate Similarity	NPC472099
0.7579	Intermediate Similarity	NPC19692
0.7579	Intermediate Similarity	NPC220151
0.7566	Intermediate Similarity	NPC55493
0.7565	Intermediate Similarity	NPC249040
0.7553	Intermediate Similarity	NPC329858
0.7553	Intermediate Similarity	NPC314333
0.7545	Intermediate Similarity	NPC104483
0.7527	Intermediate Similarity	NPC203754
0.7527	Intermediate Similarity	NPC121903
0.7527	Intermediate Similarity	NPC150048
0.7514	Intermediate Similarity	NPC19679
0.75	Intermediate Similarity	NPC264176
0.7488	Intermediate Similarity	NPC174788
0.7487	Intermediate Similarity	NPC162730
0.7487	Intermediate Similarity	NPC126066
0.7486	Intermediate Similarity	NPC211997
0.7473	Intermediate Similarity	NPC469938
0.7472	Intermediate Similarity	NPC271797
0.7472	Intermediate Similarity	NPC21174
0.7459	Intermediate Similarity	NPC158129
0.7446	Intermediate Similarity	NPC219336
0.7443	Intermediate Similarity	NPC129721
0.7435	Intermediate Similarity	NPC247735
0.7435	Intermediate Similarity	NPC472295
0.7435	Intermediate Similarity	NPC269886
0.7435	Intermediate Similarity	NPC81802
0.7435	Intermediate Similarity	NPC472210
0.7432	Intermediate Similarity	NPC134586
0.7416	Intermediate Similarity	NPC33949
0.7402	Intermediate Similarity	NPC82070
0.7401	Intermediate Similarity	NPC221786
0.7401	Intermediate Similarity	NPC474880
0.74	Intermediate Similarity	NPC475422
0.7398	Intermediate Similarity	NPC474116
0.7394	Intermediate Similarity	NPC311858
0.7391	Intermediate Similarity	NPC183662
0.7391	Intermediate Similarity	NPC15573
0.7391	Intermediate Similarity	NPC217372
0.7389	Intermediate Similarity	NPC476114
0.7387	Intermediate Similarity	NPC87755
0.7371	Intermediate Similarity	NPC102008
0.7371	Intermediate Similarity	NPC149708
0.7368	Intermediate Similarity	NPC95783
0.7368	Intermediate Similarity	NPC476492
0.736	Intermediate Similarity	NPC229173
0.7356	Intermediate Similarity	NPC40070
0.7356	Intermediate Similarity	NPC21638
0.7337	Intermediate Similarity	NPC88097
0.7337	Intermediate Similarity	NPC477065
0.733	Intermediate Similarity	NPC473763
0.733	Intermediate Similarity	NPC117244
0.7317	Intermediate Similarity	NPC281049
0.731	Intermediate Similarity	NPC193761
0.731	Intermediate Similarity	NPC476874
0.7308	Intermediate Similarity	NPC475271
0.7296	Intermediate Similarity	NPC214428
0.7291	Intermediate Similarity	NPC472291
0.7288	Intermediate Similarity	NPC285469
0.7287	Intermediate Similarity	NPC472294
0.7286	Intermediate Similarity	NPC277350
0.7273	Intermediate Similarity	NPC71037
0.7264	Intermediate Similarity	NPC469589
0.7253	Intermediate Similarity	NPC469462
0.7245	Intermediate Similarity	NPC241024
0.724	Intermediate Similarity	NPC129909
0.7234	Intermediate Similarity	NPC159125
0.7234	Intermediate Similarity	NPC469358
0.7231	Intermediate Similarity	NPC469736
0.7225	Intermediate Similarity	NPC470440
0.722	Intermediate Similarity	NPC152768
0.722	Intermediate Similarity	NPC148183
0.7213	Intermediate Similarity	NPC474897
0.7207	Intermediate Similarity	NPC475990
0.7204	Intermediate Similarity	NPC145885
0.7204	Intermediate Similarity	NPC14113
0.7204	Intermediate Similarity	NPC84827
0.7198	Intermediate Similarity	NPC49954
0.7198	Intermediate Similarity	NPC474561
0.7196	Intermediate Similarity	NPC470003
0.7182	Intermediate Similarity	NPC478182
0.7182	Intermediate Similarity	NPC311276
0.7178	Intermediate Similarity	NPC478158
0.7178	Intermediate Similarity	NPC477548
0.7175	Intermediate Similarity	NPC281094
0.7175	Intermediate Similarity	NPC478076
0.7166	Intermediate Similarity	NPC248462
0.7165	Intermediate Similarity	NPC473178
0.7164	Intermediate Similarity	NPC53344
0.715	Intermediate Similarity	NPC243716
0.7143	Intermediate Similarity	NPC470508
0.7143	Intermediate Similarity	NPC21605
0.7135	Intermediate Similarity	NPC207726
0.7135	Intermediate Similarity	NPC161861
0.7135	Intermediate Similarity	NPC476425
0.7135	Intermediate Similarity	NPC476219
0.7129	Intermediate Similarity	NPC471506
0.7127	Intermediate Similarity	NPC16667
0.712	Intermediate Similarity	NPC235684
0.712	Intermediate Similarity	NPC65080
0.7113	Intermediate Similarity	NPC472292
0.7104	Intermediate Similarity	NPC160105
0.7104	Intermediate Similarity	NPC54988
0.7101	Intermediate Similarity	NPC198988
0.7088	Intermediate Similarity	NPC476446
0.7088	Intermediate Similarity	NPC469813
0.7088	Intermediate Similarity	NPC78375
0.7087	Intermediate Similarity	NPC478157
0.7086	Intermediate Similarity	NPC478186
0.7079	Intermediate Similarity	NPC323927
0.7077	Intermediate Similarity	NPC198673
0.7073	Intermediate Similarity	NPC318299
0.7073	Intermediate Similarity	NPC475778
0.7065	Intermediate Similarity	NPC264166
0.7065	Intermediate Similarity	NPC274291
0.7065	Intermediate Similarity	NPC47059
0.7065	Intermediate Similarity	NPC63751
0.7065	Intermediate Similarity	NPC118832
0.7065	Intermediate Similarity	NPC165349
0.7065	Intermediate Similarity	NPC329708
0.7062	Intermediate Similarity	NPC64216
0.7059	Intermediate Similarity	NPC280852
0.7059	Intermediate Similarity	NPC234999
0.7059	Intermediate Similarity	NPC56618
0.7059	Intermediate Similarity	NPC84347
0.7059	Intermediate Similarity	NPC325252
0.7059	Intermediate Similarity	NPC267885
0.7053	Intermediate Similarity	NPC251936
0.7052	Intermediate Similarity	NPC473868
0.7052	Intermediate Similarity	NPC63157

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 NPC472104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	535
0.2-0.3	692
0.3-0.4	1759
0.4-0.5	2866
0.5-0.6	2351
0.6-0.7	708
0.7-0.8	56
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
0.8128	Intermediate Similarity	NPD4500	Approved
0.8128	Intermediate Similarity	NPD4501	Approved
0.8054	Intermediate Similarity	NPD4602	Approved
0.8032	Intermediate Similarity	NPD4600	Approved
0.8032	Intermediate Similarity	NPD4601	Approved
0.7979	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD5104	Approved
0.776	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2915	Discontinued
0.7624	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5075	Discontinued
0.7553	Intermediate Similarity	NPD4499	Approved
0.7543	Intermediate Similarity	NPD4326	Phase 2
0.7525	Intermediate Similarity	NPD4520	Approved
0.75	Intermediate Similarity	NPD5899	Approved
0.75	Intermediate Similarity	NPD5897	Approved
0.75	Intermediate Similarity	NPD5898	Approved
0.7461	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3385	Approved
0.7412	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4334	Discontinued
0.7396	Intermediate Similarity	NPD7944	Discontinued
0.7394	Intermediate Similarity	NPD5444	Phase 1
0.7374	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD53	Approved
0.7371	Intermediate Similarity	NPD7777	Approved
0.7371	Intermediate Similarity	NPD7778	Approved
0.7333	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD750	Phase 2
0.7316	Intermediate Similarity	NPD7234	Approved
0.7316	Intermediate Similarity	NPD7233	Approved
0.7304	Intermediate Similarity	NPD3393	Approved
0.7304	Intermediate Similarity	NPD3394	Approved
0.7304	Intermediate Similarity	NPD3389	Approved
0.7286	Intermediate Similarity	NPD7957	Phase 1
0.7286	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4397	Phase 1
0.7268	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6227	Discontinued
0.724	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6452	Discontinued
0.7216	Intermediate Similarity	NPD2882	Phase 1
0.7214	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3654	Approved
0.7202	Intermediate Similarity	NPD4315	Phase 2
0.7188	Intermediate Similarity	NPD6281	Approved
0.7184	Intermediate Similarity	NPD1683	Approved
0.7182	Intermediate Similarity	NPD6635	Approved
0.7179	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4639	Approved
0.7158	Intermediate Similarity	NPD5862	Discovery
0.7158	Intermediate Similarity	NPD4638	Approved
0.7158	Intermediate Similarity	NPD4640	Approved
0.7157	Intermediate Similarity	NPD6248	Phase 2
0.7157	Intermediate Similarity	NPD6249	Phase 2
0.7151	Intermediate Similarity	NPD5020	Approved
0.7143	Intermediate Similarity	NPD6206	Phase 1
0.7143	Intermediate Similarity	NPD4547	Phase 3
0.7143	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4418	Discontinued
0.7119	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6158	Phase 2
0.7107	Intermediate Similarity	NPD6261	Phase 3
0.7105	Intermediate Similarity	NPD4957	Phase 2
0.709	Intermediate Similarity	NPD8408	Discontinued
0.709	Intermediate Similarity	NPD4203	Approved
0.709	Intermediate Similarity	NPD4204	Approved
0.7083	Intermediate Similarity	NPD2383	Phase 1
0.7065	Intermediate Similarity	NPD4036	Approved
0.7065	Intermediate Similarity	NPD4034	Approved
0.7065	Intermediate Similarity	NPD32	Approved
0.7065	Intermediate Similarity	NPD4035	Approved
0.7065	Intermediate Similarity	NPD4122	Approved
0.7065	Intermediate Similarity	NPD4039	Approved
0.7065	Intermediate Similarity	NPD4037	Approved
0.7065	Intermediate Similarity	NPD4038	Approved
0.7065	Intermediate Similarity	NPD31	Approved
0.7065	Intermediate Similarity	NPD4033	Approved
0.7056	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5003	Discontinued
0.7056	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2094	Phase 2
0.7053	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2092	Phase 2
0.7053	Intermediate Similarity	NPD2095	Phase 2
0.7049	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6182	Approved
0.7043	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD43	Approved
0.7041	Intermediate Similarity	NPD4427	Phase 2
0.7035	Intermediate Similarity	NPD6479	Discontinued
0.7028	Intermediate Similarity	NPD7271	Approved
0.7027	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6554	Approved
0.7018	Intermediate Similarity	NPD45	Approved
0.7016	Intermediate Similarity	NPD6178	Phase 3
0.7016	Intermediate Similarity	NPD2096	Phase 2
0.7016	Intermediate Similarity	NPD2091	Phase 2
0.7011	Intermediate Similarity	NPD4047	Discontinued
0.7005	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD482	Approved
0.7	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8021	Approved
0.6995	Remote Similarity	NPD8020	Approved
0.6991	Remote Similarity	NPD7797	Approved
0.6991	Remote Similarity	NPD7796	Approved
0.699	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4120	Approved
0.6983	Remote Similarity	NPD4121	Phase 3
0.698	Remote Similarity	NPD8115	Approved
0.698	Remote Similarity	NPD8114	Approved
0.6979	Remote Similarity	NPD5555	Phase 1
0.6974	Remote Similarity	NPD5913	Phase 3
0.6974	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2382	Approved
0.6968	Remote Similarity	NPD5501	Discontinued
0.6968	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2381	Approved
0.6968	Remote Similarity	NPD2380	Approved
0.6963	Remote Similarity	NPD7730	Approved
0.6963	Remote Similarity	NPD7731	Approved
0.6961	Remote Similarity	NPD2509	Approved
0.6961	Remote Similarity	NPD7665	Phase 2
0.6961	Remote Similarity	NPD7666	Phase 3
0.6961	Remote Similarity	NPD2510	Approved
0.695	Remote Similarity	NPD5427	Suspended
0.6944	Remote Similarity	NPD5743	Approved
0.6944	Remote Similarity	NPD5742	Approved
0.6944	Remote Similarity	NPD5741	Approved
0.6938	Remote Similarity	NPD8325	Phase 3
0.6938	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD8326	Phase 3
0.6931	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5487	Phase 1
0.6931	Remote Similarity	NPD2144	Approved
0.6931	Remote Similarity	NPD7111	Discontinued
0.6931	Remote Similarity	NPD8072	Approved
0.6927	Remote Similarity	NPD7482	Phase 2
0.6927	Remote Similarity	NPD7483	Phase 2
0.6923	Remote Similarity	NPD8063	Discontinued
0.6923	Remote Similarity	NPD4897	Phase 2
0.6919	Remote Similarity	NPD7935	Phase 2
0.6919	Remote Similarity	NPD6550	Discontinued
0.6919	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6492	Phase 2
0.6912	Remote Similarity	NPD7222	Phase 2
0.6911	Remote Similarity	NPD3038	Discontinued
0.6907	Remote Similarity	NPD4948	Discontinued
0.6898	Remote Similarity	NPD7824	Approved
0.6895	Remote Similarity	NPD5891	Approved
0.6893	Remote Similarity	NPD7469	Discontinued
0.6891	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5021	Discontinued
0.6881	Remote Similarity	NPD7789	Approved
0.6881	Remote Similarity	NPD7790	Approved
0.6881	Remote Similarity	NPD7952	Approved
0.6881	Remote Similarity	NPD7791	Approved
0.6881	Remote Similarity	NPD7953	Approved
0.6881	Remote Similarity	NPD7951	Approved
0.6881	Remote Similarity	NPD7950	Approved
0.6875	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2582	Approved
0.6868	Remote Similarity	NPD2581	Approved
0.6866	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7001	Phase 3
0.6859	Remote Similarity	NPD6595	Phase 3
0.6854	Remote Similarity	NPD4702	Approved
0.6854	Remote Similarity	NPD4703	Approved
0.6853	Remote Similarity	NPD5505	Discontinued
0.6851	Remote Similarity	NPD6285	Phase 2
0.6847	Remote Similarity	NPD6176	Phase 1
0.6845	Remote Similarity	NPD1326	Approved
0.6845	Remote Similarity	NPD1325	Approved
0.6842	Remote Similarity	NPD8123	Approved
0.6842	Remote Similarity	NPD6642	Approved
0.6842	Remote Similarity	NPD8122	Approved
0.6842	Remote Similarity	NPD6641	Approved
0.6837	Remote Similarity	NPD2565	Phase 2
0.6837	Remote Similarity	NPD2564	Approved
0.6834	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD3477	Phase 2
0.6832	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5255	Approved
0.6828	Remote Similarity	NPD4554	Clinical (unspecified phase)

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