NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	662.38
Volume:	693.467
LogP:	6.635
LogD:	5.084
LogS:	-5.569
# Rotatable Bonds:	5
TPSA:	86.9
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	10
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	7.105
Fsp3:	0.561
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.488
MDCK Permeability:	1.907529804157093e-05
Pgp-inhibitor:	0.176
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.717
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.785
Plasma Protein Binding (PPB):	89.88713836669922%
Volume Distribution (VD):	2.105
Pgp-substrate:	7.81544828414917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.515
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.218
CYP2D6-inhibitor:	0.888
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.939

ADMET: Excretion

Clearance (CL):	7.016
Half-life (T1/2):	0.029

ADMET: Toxicity

hERG Blockers:	0.929
Human Hepatotoxicity (H-HT):	0.736
Drug-inuced Liver Injury (DILI):	0.382
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.097
Carcinogencity:	0.589
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC478083

Natural Product ID:	NPC478083
*Common Name:**	VNPNTCIULDUSTQ-HVIOGEPBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VNPNTCIULDUSTQ-HVIOGEPBSA-N
Standard InCHI:	InChI=1S/C41H50N4O4/c1-6-23-14-22-15-31-38(23)45(20-22)13-12-41(31)39(46)30-19-35(48-4)27(17-33(30)43-41)28-16-26-24(7-2)21-44(3)34(36(26)40(47)49-5)18-29-25-10-8-9-11-32(25)42-37(28)29/h7-11,17,19,22-23,26,28,31,34,36,38,42-43H,6,12-16,18,20-21H2,1-5H3/b24-7-/t22-,23-,26+,28+,31+,34-,36-,38-,41-/m0/s1
SMILES:	CC[C@H]1C[C@@H]2CN3[C@@H]1[C@@H](C2)[C@]1(CC3)Nc2c(C1=O)cc(c(c2)[C@H]1C[C@@H]2/C(=CC)/CN([C@H]([C@H]2C(=O)OC)Cc2c1[nH]c1c2cccc1)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581906
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002744] Vobasan 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
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	13

Activity Type	# Activity
Cell Line	10
CELL-LINE	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1210.0	nM	PMID[453823]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1060.0	nM	PMID[453823]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	8800.0	nM	PMID[453824]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	10000.0	nM	PMID[453824]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9400.0	nM	PMID[453824]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	7700.0	nM	PMID[453824]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9100.0	nM	PMID[453824]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	7100.0	nM	PMID[453824]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2900.0	nM	PMID[453824]
NPT22764	CELL-LINE	KB/VJ300	Homo sapiens	IC50	=	9100.0	nM	PMID[453824]
NPT2	Others	Unspecified		IC50	=	8300.0	nM	PMID[453824]
NPT22764	CELL-LINE	KB/VJ300	Homo sapiens	IC50	=	3300.0	nM	PMID[453824]

☑ 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 NPC478083 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	576
0.1-0.2	2584
0.2-0.3	10670
0.3-0.4	9754
0.4-0.5	13910
0.5-0.6	3050
0.6-0.7	1872
0.7-0.8	229
0.8-0.85	35
0.85-0.9	15
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC17437
0.9083	High Similarity	NPC477067
0.9083	High Similarity	NPC478082
0.9039	High Similarity	NPC477066
0.9	High Similarity	NPC478081
0.8703	High Similarity	NPC478080
0.8675	High Similarity	NPC473540
0.8523	High Similarity	NPC81939
0.8487	Intermediate Similarity	NPC475666
0.8478	Intermediate Similarity	NPC478078
0.821	Intermediate Similarity	NPC96321
0.8062	Intermediate Similarity	NPC471304
0.8057	Intermediate Similarity	NPC329982
0.8051	Intermediate Similarity	NPC311906
0.7983	Intermediate Similarity	NPC472099
0.7965	Intermediate Similarity	NPC148183
0.7965	Intermediate Similarity	NPC152768
0.7949	Intermediate Similarity	NPC280799
0.7907	Intermediate Similarity	NPC471303
0.7885	Intermediate Similarity	NPC300156
0.7875	Intermediate Similarity	NPC474192
0.7875	Intermediate Similarity	NPC475720
0.7857	Intermediate Similarity	NPC157931
0.7835	Intermediate Similarity	NPC472098
0.7826	Intermediate Similarity	NPC191489
0.7821	Intermediate Similarity	NPC473041
0.7802	Intermediate Similarity	NPC478074
0.7773	Intermediate Similarity	NPC100734
0.7773	Intermediate Similarity	NPC477065
0.7773	Intermediate Similarity	NPC88923
0.7773	Intermediate Similarity	NPC315634
0.7737	Intermediate Similarity	NPC39370
0.7735	Intermediate Similarity	NPC469928
0.7717	Intermediate Similarity	NPC284685
0.7683	Intermediate Similarity	NPC475816
0.7665	Intermediate Similarity	NPC329793
0.7657	Intermediate Similarity	NPC322482
0.7654	Intermediate Similarity	NPC473186
0.7652	Intermediate Similarity	NPC45190
0.7642	Intermediate Similarity	NPC101350
0.7638	Intermediate Similarity	NPC53534
0.7627	Intermediate Similarity	NPC305984
0.7625	Intermediate Similarity	NPC21638
0.7602	Intermediate Similarity	NPC235685
0.76	Intermediate Similarity	NPC469734
0.7582	Intermediate Similarity	NPC49547
0.7576	Intermediate Similarity	NPC195788
0.7576	Intermediate Similarity	NPC237901
0.7562	Intermediate Similarity	NPC74575
0.7561	Intermediate Similarity	NPC473187
0.7559	Intermediate Similarity	NPC244543
0.7553	Intermediate Similarity	NPC169402
0.7551	Intermediate Similarity	NPC473105
0.7543	Intermediate Similarity	NPC4687
0.7542	Intermediate Similarity	NPC144452
0.7531	Intermediate Similarity	NPC471762
0.7529	Intermediate Similarity	NPC303374
0.7529	Intermediate Similarity	NPC152620
0.7521	Intermediate Similarity	NPC46561
0.75	Intermediate Similarity	NPC39500
0.749	Intermediate Similarity	NPC257851
0.749	Intermediate Similarity	NPC208522
0.748	Intermediate Similarity	NPC329631
0.747	Intermediate Similarity	NPC270515
0.7469	Intermediate Similarity	NPC474688
0.7468	Intermediate Similarity	NPC116238
0.7468	Intermediate Similarity	NPC321428
0.7463	Intermediate Similarity	NPC260909
0.7459	Intermediate Similarity	NPC274640
0.7459	Intermediate Similarity	NPC194740
0.7458	Intermediate Similarity	NPC323969
0.745	Intermediate Similarity	NPC142385
0.7449	Intermediate Similarity	NPC470018
0.7418	Intermediate Similarity	NPC470126
0.7415	Intermediate Similarity	NPC87413
0.7397	Intermediate Similarity	NPC280272
0.7393	Intermediate Similarity	NPC478075
0.739	Intermediate Similarity	NPC15801
0.7388	Intermediate Similarity	NPC66777
0.7388	Intermediate Similarity	NPC253580
0.7386	Intermediate Similarity	NPC174760
0.7375	Intermediate Similarity	NPC184408
0.7373	Intermediate Similarity	NPC470020
0.7366	Intermediate Similarity	NPC122436
0.7364	Intermediate Similarity	NPC330009
0.7346	Intermediate Similarity	NPC89549
0.7342	Intermediate Similarity	NPC208284
0.7342	Intermediate Similarity	NPC9894
0.7341	Intermediate Similarity	NPC72905
0.7338	Intermediate Similarity	NPC227824
0.7333	Intermediate Similarity	NPC63971
0.7333	Intermediate Similarity	NPC91868
0.7328	Intermediate Similarity	NPC260434
0.7328	Intermediate Similarity	NPC132385
0.732	Intermediate Similarity	NPC6786
0.7319	Intermediate Similarity	NPC249583
0.7314	Intermediate Similarity	NPC276657
0.7314	Intermediate Similarity	NPC225279
0.7311	Intermediate Similarity	NPC308137
0.7311	Intermediate Similarity	NPC310211
0.7302	Intermediate Similarity	NPC148889
0.7302	Intermediate Similarity	NPC475844
0.7298	Intermediate Similarity	NPC207686
0.7294	Intermediate Similarity	NPC218388
0.7291	Intermediate Similarity	NPC41679
0.7284	Intermediate Similarity	NPC198503
0.7284	Intermediate Similarity	NPC329747
0.728	Intermediate Similarity	NPC477549
0.7276	Intermediate Similarity	NPC137353
0.7273	Intermediate Similarity	NPC74360
0.7269	Intermediate Similarity	NPC22481
0.7269	Intermediate Similarity	NPC187501
0.7258	Intermediate Similarity	NPC477531
0.7255	Intermediate Similarity	NPC178858
0.7251	Intermediate Similarity	NPC470022
0.7251	Intermediate Similarity	NPC184680
0.7249	Intermediate Similarity	NPC472210
0.7249	Intermediate Similarity	NPC269886
0.7249	Intermediate Similarity	NPC247735
0.7249	Intermediate Similarity	NPC81802
0.7249	Intermediate Similarity	NPC472295
0.7247	Intermediate Similarity	NPC252251
0.7243	Intermediate Similarity	NPC150239
0.7243	Intermediate Similarity	NPC477533
0.7238	Intermediate Similarity	NPC473180
0.7238	Intermediate Similarity	NPC94157
0.7224	Intermediate Similarity	NPC51388
0.7222	Intermediate Similarity	NPC470785
0.7222	Intermediate Similarity	NPC470784
0.722	Intermediate Similarity	NPC183407
0.7218	Intermediate Similarity	NPC24019
0.7218	Intermediate Similarity	NPC209174
0.7215	Intermediate Similarity	NPC39679
0.7215	Intermediate Similarity	NPC475910
0.721	Intermediate Similarity	NPC249040
0.7206	Intermediate Similarity	NPC314222
0.7206	Intermediate Similarity	NPC196449
0.7202	Intermediate Similarity	NPC208084
0.7197	Intermediate Similarity	NPC220337
0.7191	Intermediate Similarity	NPC476098
0.7189	Intermediate Similarity	NPC475253
0.7185	Intermediate Similarity	NPC476116
0.7184	Intermediate Similarity	NPC210434
0.7183	Intermediate Similarity	NPC189903
0.7183	Intermediate Similarity	NPC182907
0.7178	Intermediate Similarity	NPC118228
0.7177	Intermediate Similarity	NPC314954
0.7177	Intermediate Similarity	NPC33949
0.7167	Intermediate Similarity	NPC264176
0.7166	Intermediate Similarity	NPC227908
0.7161	Intermediate Similarity	NPC132539
0.716	Intermediate Similarity	NPC303658
0.716	Intermediate Similarity	NPC247803
0.7149	Intermediate Similarity	NPC102338
0.7149	Intermediate Similarity	NPC63199
0.7149	Intermediate Similarity	NPC111602
0.7149	Intermediate Similarity	NPC278525
0.7149	Intermediate Similarity	NPC3207
0.7149	Intermediate Similarity	NPC196251
0.7143	Intermediate Similarity	NPC470017
0.7143	Intermediate Similarity	NPC131017
0.7143	Intermediate Similarity	NPC108342
0.7143	Intermediate Similarity	NPC133609
0.7137	Intermediate Similarity	NPC160381
0.7131	Intermediate Similarity	NPC288987
0.7126	Intermediate Similarity	NPC471583
0.7126	Intermediate Similarity	NPC115588
0.7126	Intermediate Similarity	NPC471782
0.712	Intermediate Similarity	NPC474701
0.7119	Intermediate Similarity	NPC162484
0.7118	Intermediate Similarity	NPC329858
0.7115	Intermediate Similarity	NPC189079
0.7114	Intermediate Similarity	NPC216612
0.7113	Intermediate Similarity	NPC201697
0.7112	Intermediate Similarity	NPC472293
0.7112	Intermediate Similarity	NPC472116
0.7104	Intermediate Similarity	NPC26543
0.7104	Intermediate Similarity	NPC165964
0.7102	Intermediate Similarity	NPC86078
0.7101	Intermediate Similarity	NPC193777
0.7101	Intermediate Similarity	NPC270918
0.7095	Intermediate Similarity	NPC473493
0.7092	Intermediate Similarity	NPC196718
0.7092	Intermediate Similarity	NPC207620
0.7092	Intermediate Similarity	NPC102593
0.7092	Intermediate Similarity	NPC139373
0.7087	Intermediate Similarity	NPC278540
0.7083	Intermediate Similarity	NPC234999
0.708	Intermediate Similarity	NPC176127
0.7077	Intermediate Similarity	NPC473800
0.7077	Intermediate Similarity	NPC473188
0.7076	Intermediate Similarity	NPC162730
0.7075	Intermediate Similarity	NPC295228
0.7073	Intermediate Similarity	NPC60621
0.7073	Intermediate Similarity	NPC477532
0.7069	Intermediate Similarity	NPC276517
0.7068	Intermediate Similarity	NPC473185
0.7067	Intermediate Similarity	NPC169716
0.7066	Intermediate Similarity	NPC469592
0.7066	Intermediate Similarity	NPC471080

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 NPC478083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	626
0.2-0.3	932
0.3-0.4	1723
0.4-0.5	2766
0.5-0.6	2035
0.6-0.7	695
0.7-0.8	82
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD8358	Approved
0.7826	Intermediate Similarity	NPD7708	Approved
0.7773	Intermediate Similarity	NPD7803	Approved
0.7752	Intermediate Similarity	NPD8364	Approved
0.7752	Intermediate Similarity	NPD8363	Approved
0.7717	Intermediate Similarity	NPD7956	Approved
0.7717	Intermediate Similarity	NPD7955	Approved
0.7692	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6242	Discontinued
0.7671	Intermediate Similarity	NPD5488	Discontinued
0.766	Intermediate Similarity	NPD3393	Approved
0.766	Intermediate Similarity	NPD3389	Approved
0.766	Intermediate Similarity	NPD3394	Approved
0.7654	Intermediate Similarity	NPD4885	Approved
0.7631	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD8466	Approved
0.7576	Intermediate Similarity	NPD8465	Approved
0.7576	Intermediate Similarity	NPD8467	Approved
0.7572	Intermediate Similarity	NPD4952	Phase 3
0.7562	Intermediate Similarity	NPD7994	Phase 2
0.7562	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD8091	Phase 3
0.7528	Intermediate Similarity	NPD8425	Approved
0.7528	Intermediate Similarity	NPD8426	Approved
0.7521	Intermediate Similarity	NPD5632	Approved
0.7509	Intermediate Similarity	NPD8427	Approved
0.7509	Intermediate Similarity	NPD8429	Approved
0.7509	Intermediate Similarity	NPD8428	Approved
0.7489	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD4373	Phase 2
0.7463	Intermediate Similarity	NPD8460	Approved
0.7463	Intermediate Similarity	NPD8459	Approved
0.744	Intermediate Similarity	NPD6790	Phase 1
0.7429	Intermediate Similarity	NPD5479	Discontinued
0.7422	Intermediate Similarity	NPD8463	Approved
0.7419	Intermediate Similarity	NPD3006	Discontinued
0.74	Intermediate Similarity	NPD8016	Phase 3
0.74	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5482	Discontinued
0.7362	Intermediate Similarity	NPD2509	Approved
0.7362	Intermediate Similarity	NPD2510	Approved
0.7342	Intermediate Similarity	NPD5416	Discontinued
0.7333	Intermediate Similarity	NPD8102	Discontinued
0.7331	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7688	Phase 1
0.7325	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5293	Phase 2
0.7287	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7853	Phase 2
0.728	Intermediate Similarity	NPD6531	Approved
0.728	Intermediate Similarity	NPD6530	Approved
0.7276	Intermediate Similarity	NPD3259	Approved
0.7276	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4558	Phase 2
0.725	Intermediate Similarity	NPD3257	Approved
0.725	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7417	Discontinued
0.7231	Intermediate Similarity	NPD4429	Discontinued
0.7229	Intermediate Similarity	NPD7797	Approved
0.7229	Intermediate Similarity	NPD7796	Approved
0.7215	Intermediate Similarity	NPD5658	Approved
0.7202	Intermediate Similarity	NPD6770	Approved
0.7202	Intermediate Similarity	NPD3258	Approved
0.719	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.718	Intermediate Similarity	NPD7925	Phase 2
0.718	Intermediate Similarity	NPD7924	Phase 2
0.7178	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8489	Phase 1
0.716	Intermediate Similarity	NPD7395	Discontinued
0.7154	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7454	Approved
0.7095	Intermediate Similarity	NPD7455	Approved
0.7075	Intermediate Similarity	NPD5891	Approved
0.707	Intermediate Similarity	NPD6716	Phase 1
0.7069	Intermediate Similarity	NPD4418	Discontinued
0.7064	Intermediate Similarity	NPD4501	Approved
0.7064	Intermediate Similarity	NPD4500	Approved
0.7054	Intermediate Similarity	NPD8100	Phase 3
0.7046	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7219	Approved
0.7045	Intermediate Similarity	NPD7221	Approved
0.7041	Intermediate Similarity	NPD5450	Discontinued
0.7	Intermediate Similarity	NPD2916	Discontinued
0.7	Intermediate Similarity	NPD4328	Approved
0.7	Intermediate Similarity	NPD6376	Discontinued
0.6992	Remote Similarity	NPD7404	Approved
0.6989	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5530	Phase 1
0.6984	Remote Similarity	NPD6962	Phase 2
0.6983	Remote Similarity	NPD7470	Discontinued
0.6983	Remote Similarity	NPD5475	Discontinued
0.6976	Remote Similarity	NPD6995	Phase 1
0.6973	Remote Similarity	NPD8101	Phase 3
0.697	Remote Similarity	NPD4499	Approved
0.6961	Remote Similarity	NPD8524	Approved
0.6955	Remote Similarity	NPD8096	Phase 3
0.6955	Remote Similarity	NPD8097	Phase 3
0.6955	Remote Similarity	NPD5866	Approved
0.6955	Remote Similarity	NPD6228	Discontinued
0.6948	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3947	Discontinued
0.6944	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5022	Discontinued
0.6939	Remote Similarity	NPD8160	Phase 2
0.6923	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4368	Phase 2
0.6908	Remote Similarity	NPD6209	Approved
0.6902	Remote Similarity	NPD2951	Discontinued
0.6901	Remote Similarity	NPD4506	Discontinued
0.6892	Remote Similarity	NPD8289	Discontinued
0.689	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD5429	Discontinued
0.6888	Remote Similarity	NPD7222	Phase 2
0.6885	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1038	Approved
0.688	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6873	Remote Similarity	NPD7392	Phase 2
0.686	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4561	Discontinued
0.6857	Remote Similarity	NPD3945	Discontinued
0.6855	Remote Similarity	NPD7194	Discontinued
0.6853	Remote Similarity	NPD3925	Approved
0.685	Remote Similarity	NPD7689	Approved
0.6849	Remote Similarity	NPD484	Approved
0.6849	Remote Similarity	NPD4601	Approved
0.6849	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4600	Approved
0.6846	Remote Similarity	NPD8403	Phase 1
0.6846	Remote Similarity	NPD3003	Approved
0.6827	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3354	Phase 2
0.6815	Remote Similarity	NPD7878	Phase 2
0.6805	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5901	Discontinued
0.6805	Remote Similarity	NPD4795	Phase 2
0.6803	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5507	Approved
0.68	Remote Similarity	NPD5506	Approved
0.6798	Remote Similarity	NPD4845	Discontinued
0.6798	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7951	Approved
0.6797	Remote Similarity	NPD7790	Approved
0.6797	Remote Similarity	NPD7950	Approved
0.6797	Remote Similarity	NPD7953	Approved
0.6797	Remote Similarity	NPD7791	Approved
0.6797	Remote Similarity	NPD7789	Approved
0.6797	Remote Similarity	NPD7952	Approved
0.6793	Remote Similarity	NPD5003	Discontinued
0.6792	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD5519	Discontinued
0.6787	Remote Similarity	NPD3763	Approved
0.678	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7010	Phase 3
0.6772	Remote Similarity	NPD5559	Phase 2
0.6769	Remote Similarity	NPD5473	Discontinued
0.6766	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6176	Phase 1
0.6761	Remote Similarity	NPD5903	Approved
0.6761	Remote Similarity	NPD5902	Approved
0.676	Remote Similarity	NPD5930	Phase 3
0.6758	Remote Similarity	NPD3746	Discontinued
0.6757	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6456	Discontinued
0.6748	Remote Similarity	NPD7069	Discontinued
0.6747	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7658	Phase 2
0.6738	Remote Similarity	NPD8525	Approved
0.6738	Remote Similarity	NPD4948	Discontinued
0.6736	Remote Similarity	NPD8115	Approved
0.6736	Remote Similarity	NPD7176	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD8114	Approved
0.6734	Remote Similarity	NPD5612	Discontinued
0.6732	Remote Similarity	NPD7558	Phase 2
0.6731	Remote Similarity	NPD7885	Phase 2
0.6731	Remote Similarity	NPD7886	Phase 2
0.6723	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5913	Phase 3
0.6721	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD3986	Discontinued
0.6714	Remote Similarity	NPD7766	Phase 2
0.6708	Remote Similarity	NPD3507	Phase 2
0.6705	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6276	Discontinued
0.6703	Remote Similarity	NPD6773	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