NPASS Compound

Structure

CID17374 OpenBabel06191715342D 31 31 0 0 1 0 0 0 0 0999 V2000 8.6603 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 8.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 21 1 0 0 0 0 3 28 1 0 0 0 0 4 31 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 21 1 0 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 22 24 1 0 0 0 0 23 15 1 6 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 25 29 2 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	449.27
Volume:	486.455
LogP:	6.192
LogD:	4.419
LogS:	-5.226
# Rotatable Bonds:	16
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	3.511
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.602
MDCK Permeability:	2.1663263396476395e-05
Pgp-inhibitor:	0.758
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.155
30% Bioavailability (F30%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.312
Plasma Protein Binding (PPB):	99.18611907958984%
Volume Distribution (VD):	0.24
Pgp-substrate:	1.2173625230789185%

ADMET: Metabolism

CYP1A2-inhibitor:	0.211
CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.637
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.497
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.842
CYP2D6-substrate:	0.704
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	4.027
Half-life (T1/2):	0.42

ADMET: Toxicity

hERG Blockers:	0.219
Human Hepatotoxicity (H-HT):	0.568
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.951
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.799

Download Data

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

Natural Product: NPC17374

Natural Product ID:	NPC17374
*Common Name:**	Malyngamide M
IUPAC Name:	(E,7S)-N-[(E)-3-chloro-2-(2-hydroxy-3-methylphenyl)prop-2-enyl]-7-methoxy-N-methyltetradec-4-enamide
Synonyms:	Malyngamide M
Standard InCHIKey:	ONLRPLDTZJYMBK-MHZFXPHZSA-N
Standard InCHI:	InChI=1S/C26H40ClNO3/c1-5-6-7-8-10-15-23(31-4)16-11-9-12-18-25(29)28(3)20-22(19-27)24-17-13-14-21(2)26(24)30/h9,11,13-14,17,19,23,30H,5-8,10,12,15-16,18,20H2,1-4H3/b11-9+,22-19-/t23-/m0/s1
SMILES:	CCCCCCC[C@@H](C/C=C/CCC(=O)N(C/C(=C/Cl)/c1cccc(c1O)C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495850
PubChem CID:	10623415
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001272] Cresols [CHEMONTID:0001274] Ortho cresols

*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
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25612070]
NPO11922	Gracilaria coronopifolia	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8843576]
NPO11922	Gracilaria coronopifolia	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548841]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	stem	n.a.	Database[Article]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16525	Luvunga eleutherandra	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15408	Ophryosporus heptanthus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13880	Iris clarkei	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14059	Dickeya zeae	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11922	Gracilaria coronopifolia	Species	Gracilariaceae	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
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		IC50	>	20000.0	nM	PMID[520813]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[520814]

☑ 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 NPC17374 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	125
0.1-0.2	931
0.2-0.3	4544
0.3-0.4	13348
0.4-0.5	10780
0.5-0.6	11122
0.6-0.7	1814
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.773	Intermediate Similarity	NPC150712
0.7591	Intermediate Similarity	NPC283079
0.7574	Intermediate Similarity	NPC218323
0.7447	Intermediate Similarity	NPC473360
0.7445	Intermediate Similarity	NPC476353
0.7397	Intermediate Similarity	NPC81026
0.7357	Intermediate Similarity	NPC257390
0.7329	Intermediate Similarity	NPC266741
0.7317	Intermediate Similarity	NPC155847
0.7317	Intermediate Similarity	NPC289381
0.731	Intermediate Similarity	NPC251439
0.7299	Intermediate Similarity	NPC171372
0.7286	Intermediate Similarity	NPC120251
0.7226	Intermediate Similarity	NPC307020
0.7209	Intermediate Similarity	NPC474149
0.7171	Intermediate Similarity	NPC39431
0.7132	Intermediate Similarity	NPC258056
0.7124	Intermediate Similarity	NPC123011
0.7124	Intermediate Similarity	NPC256689
0.7121	Intermediate Similarity	NPC474050
0.7121	Intermediate Similarity	NPC474114
0.7121	Intermediate Similarity	NPC473931
0.7109	Intermediate Similarity	NPC142297
0.7097	Intermediate Similarity	NPC128723
0.708	Intermediate Similarity	NPC474862
0.7068	Intermediate Similarity	NPC10286
0.7068	Intermediate Similarity	NPC213
0.7045	Intermediate Similarity	NPC28784
0.7045	Intermediate Similarity	NPC296144
0.704	Intermediate Similarity	NPC228400
0.704	Intermediate Similarity	NPC214200
0.7034	Intermediate Similarity	NPC109580
0.7031	Intermediate Similarity	NPC231705
0.7021	Intermediate Similarity	NPC296712
0.7007	Intermediate Similarity	NPC231572
0.7	Intermediate Similarity	NPC282855
0.7	Intermediate Similarity	NPC65855
0.7	Intermediate Similarity	NPC292758
0.7	Intermediate Similarity	NPC26013
0.6977	Remote Similarity	NPC228737
0.6963	Remote Similarity	NPC137096
0.6957	Remote Similarity	NPC268348
0.6953	Remote Similarity	NPC243677
0.695	Remote Similarity	NPC305717
0.6947	Remote Similarity	NPC208229
0.6937	Remote Similarity	NPC209463
0.6934	Remote Similarity	NPC321133
0.6929	Remote Similarity	NPC178902
0.6923	Remote Similarity	NPC31274
0.6923	Remote Similarity	NPC317305
0.6923	Remote Similarity	NPC279887
0.6923	Remote Similarity	NPC68260
0.6911	Remote Similarity	NPC289769
0.6901	Remote Similarity	NPC469666
0.6897	Remote Similarity	NPC266425
0.6892	Remote Similarity	NPC476989
0.6892	Remote Similarity	NPC197921
0.6887	Remote Similarity	NPC16188
0.6884	Remote Similarity	NPC56634
0.6883	Remote Similarity	NPC262166
0.6875	Remote Similarity	NPC469479
0.6871	Remote Similarity	NPC307682
0.6871	Remote Similarity	NPC242159
0.6871	Remote Similarity	NPC313694
0.687	Remote Similarity	NPC145638
0.687	Remote Similarity	NPC75272
0.687	Remote Similarity	NPC471954
0.687	Remote Similarity	NPC290566
0.6863	Remote Similarity	NPC473491
0.6863	Remote Similarity	NPC324081
0.6849	Remote Similarity	NPC474787
0.6849	Remote Similarity	NPC9687
0.6849	Remote Similarity	NPC260045
0.6849	Remote Similarity	NPC76785
0.6849	Remote Similarity	NPC118099
0.6849	Remote Similarity	NPC90194
0.6849	Remote Similarity	NPC49577
0.6849	Remote Similarity	NPC79465
0.6849	Remote Similarity	NPC475318
0.6849	Remote Similarity	NPC293377
0.6849	Remote Similarity	NPC474811
0.6849	Remote Similarity	NPC273907
0.6849	Remote Similarity	NPC474855
0.6849	Remote Similarity	NPC475598
0.6849	Remote Similarity	NPC476102
0.6849	Remote Similarity	NPC151706
0.6846	Remote Similarity	NPC91953
0.6842	Remote Similarity	NPC228425
0.6835	Remote Similarity	NPC142577
0.6828	Remote Similarity	NPC328070
0.6824	Remote Similarity	NPC322526
0.6824	Remote Similarity	NPC471201
0.6822	Remote Similarity	NPC303141
0.6815	Remote Similarity	NPC317254
0.6812	Remote Similarity	NPC471308
0.6812	Remote Similarity	NPC160120
0.6812	Remote Similarity	NPC17388
0.6812	Remote Similarity	NPC53596
0.6812	Remote Similarity	NPC289330
0.6803	Remote Similarity	NPC6570
0.6797	Remote Similarity	NPC108497
0.6795	Remote Similarity	NPC244509
0.6795	Remote Similarity	NPC476268
0.6794	Remote Similarity	NPC24101
0.6794	Remote Similarity	NPC470039
0.6794	Remote Similarity	NPC262365
0.6794	Remote Similarity	NPC96224
0.6791	Remote Similarity	NPC190212
0.679	Remote Similarity	NPC469505
0.6783	Remote Similarity	NPC81092
0.6783	Remote Similarity	NPC8305
0.6783	Remote Similarity	NPC213969
0.6783	Remote Similarity	NPC66177
0.6783	Remote Similarity	NPC165726
0.6783	Remote Similarity	NPC268763
0.6783	Remote Similarity	NPC103605
0.6774	Remote Similarity	NPC56685
0.6772	Remote Similarity	NPC248396
0.6772	Remote Similarity	NPC129373
0.6772	Remote Similarity	NPC225506
0.6772	Remote Similarity	NPC48730
0.6757	Remote Similarity	NPC473052
0.6757	Remote Similarity	NPC316906
0.6757	Remote Similarity	NPC473055
0.6748	Remote Similarity	NPC204210
0.6746	Remote Similarity	NPC474073
0.6746	Remote Similarity	NPC77492
0.6742	Remote Similarity	NPC98392
0.6741	Remote Similarity	NPC114918
0.6739	Remote Similarity	NPC182240
0.6739	Remote Similarity	NPC319950
0.6739	Remote Similarity	NPC473767
0.6739	Remote Similarity	NPC476020
0.6738	Remote Similarity	NPC285394
0.6733	Remote Similarity	NPC469360
0.6728	Remote Similarity	NPC294516
0.6728	Remote Similarity	NPC107938
0.6721	Remote Similarity	NPC70436
0.672	Remote Similarity	NPC144682
0.672	Remote Similarity	NPC8392
0.6719	Remote Similarity	NPC327226
0.6719	Remote Similarity	NPC51015
0.6716	Remote Similarity	NPC228988
0.6716	Remote Similarity	NPC26615
0.6716	Remote Similarity	NPC286222
0.6711	Remote Similarity	NPC297322
0.671	Remote Similarity	NPC233702
0.6694	Remote Similarity	NPC94139
0.6694	Remote Similarity	NPC325292
0.6694	Remote Similarity	NPC162314
0.6694	Remote Similarity	NPC306884
0.6694	Remote Similarity	NPC407
0.6694	Remote Similarity	NPC147284
0.6694	Remote Similarity	NPC138117
0.6694	Remote Similarity	NPC210497
0.6694	Remote Similarity	NPC3358
0.6694	Remote Similarity	NPC307235
0.6693	Remote Similarity	NPC260775
0.6693	Remote Similarity	NPC216468
0.6693	Remote Similarity	NPC122005
0.6693	Remote Similarity	NPC51333
0.6693	Remote Similarity	NPC125732
0.6693	Remote Similarity	NPC252821
0.6693	Remote Similarity	NPC78119
0.6693	Remote Similarity	NPC132078
0.6692	Remote Similarity	NPC44732
0.6692	Remote Similarity	NPC99557
0.6692	Remote Similarity	NPC154899
0.6692	Remote Similarity	NPC63345
0.6692	Remote Similarity	NPC233396
0.6692	Remote Similarity	NPC219286
0.6692	Remote Similarity	NPC252544
0.6692	Remote Similarity	NPC321252
0.6692	Remote Similarity	NPC138942
0.6691	Remote Similarity	NPC474486
0.6691	Remote Similarity	NPC23402
0.6691	Remote Similarity	NPC473136
0.669	Remote Similarity	NPC474479
0.669	Remote Similarity	NPC474803
0.6686	Remote Similarity	NPC99723
0.6667	Remote Similarity	NPC470202
0.6667	Remote Similarity	NPC471228
0.6667	Remote Similarity	NPC206205
0.6667	Remote Similarity	NPC5194
0.6667	Remote Similarity	NPC471315
0.6667	Remote Similarity	NPC244336
0.6667	Remote Similarity	NPC168829
0.6667	Remote Similarity	NPC55561
0.6667	Remote Similarity	NPC125852
0.6667	Remote Similarity	NPC202198
0.6667	Remote Similarity	NPC261934
0.6667	Remote Similarity	NPC153690
0.6667	Remote Similarity	NPC68055
0.6667	Remote Similarity	NPC235762
0.6667	Remote Similarity	NPC283711
0.6667	Remote Similarity	NPC242136
0.6667	Remote Similarity	NPC471314
0.6646	Remote Similarity	NPC475204
0.6646	Remote Similarity	NPC475123
0.6646	Remote Similarity	NPC46009

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 NPC17374 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	111
0.1-0.2	534
0.2-0.3	986
0.3-0.4	2024
0.4-0.5	2793
0.5-0.6	2088
0.6-0.7	584
0.7-0.8	30
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
0.7852	Intermediate Similarity	NPD4207	Discontinued
0.7778	Intermediate Similarity	NPD4208	Discontinued
0.7424	Intermediate Similarity	NPD5304	Approved
0.7424	Intermediate Similarity	NPD5303	Approved
0.7415	Intermediate Similarity	NPD3141	Discontinued
0.7372	Intermediate Similarity	NPD1133	Approved
0.7372	Intermediate Similarity	NPD1131	Approved
0.7372	Intermediate Similarity	NPD1129	Approved
0.7372	Intermediate Similarity	NPD1135	Approved
0.7372	Intermediate Similarity	NPD1134	Approved
0.7347	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2228	Approved
0.7308	Intermediate Similarity	NPD2234	Approved
0.7308	Intermediate Similarity	NPD2229	Approved
0.7305	Intermediate Similarity	NPD6407	Approved
0.7305	Intermediate Similarity	NPD6405	Approved
0.7302	Intermediate Similarity	NPD1444	Approved
0.7302	Intermediate Similarity	NPD1445	Approved
0.7293	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3123	Discovery
0.7259	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4659	Approved
0.7218	Intermediate Similarity	NPD16	Approved
0.7218	Intermediate Similarity	NPD856	Approved
0.7181	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1792	Phase 2
0.7122	Intermediate Similarity	NPD4103	Phase 2
0.7122	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1793	Approved
0.7121	Intermediate Similarity	NPD1791	Approved
0.712	Intermediate Similarity	NPD855	Approved
0.712	Intermediate Similarity	NPD854	Approved
0.7111	Intermediate Similarity	NPD4093	Discontinued
0.7109	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1755	Approved
0.7037	Intermediate Similarity	NPD316	Approved
0.7029	Intermediate Similarity	NPD2561	Approved
0.7029	Intermediate Similarity	NPD2562	Approved
0.6986	Remote Similarity	NPD3554	Approved
0.6986	Remote Similarity	NPD3552	Approved
0.6986	Remote Similarity	NPD3555	Approved
0.6986	Remote Similarity	NPD3553	Approved
0.6985	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4818	Approved
0.6984	Remote Similarity	NPD4817	Approved
0.6967	Remote Similarity	NPD845	Approved
0.6963	Remote Similarity	NPD318	Approved
0.6963	Remote Similarity	NPD9615	Approved
0.6963	Remote Similarity	NPD9616	Approved
0.6963	Remote Similarity	NPD317	Approved
0.6963	Remote Similarity	NPD9613	Approved
0.6954	Remote Similarity	NPD6667	Approved
0.6954	Remote Similarity	NPD6666	Approved
0.6947	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2904	Discontinued
0.6937	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2667	Approved
0.6934	Remote Similarity	NPD2668	Approved
0.6912	Remote Similarity	NPD1759	Phase 1
0.6906	Remote Similarity	NPD2233	Approved
0.6906	Remote Similarity	NPD2230	Approved
0.6906	Remote Similarity	NPD2232	Approved
0.6901	Remote Similarity	NPD4212	Discontinued
0.6883	Remote Similarity	NPD7131	Phase 3
0.6871	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7030	Discontinued
0.6838	Remote Similarity	NPD1758	Phase 1
0.6828	Remote Similarity	NPD829	Discontinued
0.6818	Remote Similarity	NPD6090	Discontinued
0.6815	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1751	Approved
0.6809	Remote Similarity	NPD2079	Discontinued
0.6809	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4658	Approved
0.6797	Remote Similarity	NPD4656	Approved
0.6795	Remote Similarity	NPD6057	Approved
0.6795	Remote Similarity	NPD6056	Approved
0.6788	Remote Similarity	NPD2486	Discontinued
0.6783	Remote Similarity	NPD3637	Approved
0.6783	Remote Similarity	NPD3635	Approved
0.6783	Remote Similarity	NPD3636	Approved
0.6779	Remote Similarity	NPD4476	Approved
0.6779	Remote Similarity	NPD4477	Approved
0.6765	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3294	Phase 2
0.6757	Remote Similarity	NPD7230	Approved
0.6757	Remote Similarity	NPD7231	Approved
0.6755	Remote Similarity	NPD5177	Phase 3
0.6744	Remote Similarity	NPD9610	Approved
0.6744	Remote Similarity	NPD9608	Approved
0.6741	Remote Similarity	NPD593	Approved
0.6741	Remote Similarity	NPD9614	Approved
0.6741	Remote Similarity	NPD9618	Approved
0.6741	Remote Similarity	NPD595	Approved
0.6738	Remote Similarity	NPD1421	Approved
0.6738	Remote Similarity	NPD5157	Phase 1
0.6738	Remote Similarity	NPD5159	Phase 2
0.6738	Remote Similarity	NPD1420	Approved
0.6738	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4620	Approved
0.6736	Remote Similarity	NPD5203	Approved
0.6736	Remote Similarity	NPD5201	Approved
0.6736	Remote Similarity	NPD4617	Approved
0.672	Remote Similarity	NPD1809	Phase 2
0.6714	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD2990	Approved
0.6713	Remote Similarity	NPD2987	Approved
0.6713	Remote Similarity	NPD9723	Approved
0.6712	Remote Similarity	NPD7086	Phase 2
0.6712	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2245	Discovery
0.6711	Remote Similarity	NPD3400	Discontinued
0.6707	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD4254	Approved
0.6692	Remote Similarity	NPD4253	Approved
0.6691	Remote Similarity	NPD7725	Approved
0.6691	Remote Similarity	NPD256	Approved
0.6691	Remote Similarity	NPD255	Approved
0.669	Remote Similarity	NPD3136	Phase 2
0.669	Remote Similarity	NPD1024	Discontinued
0.669	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2238	Phase 2
0.6667	Remote Similarity	NPD6032	Approved
0.6667	Remote Similarity	NPD6894	Phase 1
0.6667	Remote Similarity	NPD3681	Approved
0.6667	Remote Similarity	NPD4231	Approved
0.6667	Remote Similarity	NPD4229	Approved
0.6667	Remote Similarity	NPD6346	Approved
0.6667	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7248	Discontinued
0.6667	Remote Similarity	NPD5699	Approved
0.6667	Remote Similarity	NPD3683	Approved
0.6667	Remote Similarity	NPD3680	Approved
0.6667	Remote Similarity	NPD7427	Discontinued
0.6667	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3682	Approved
0.6644	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2626	Approved
0.6643	Remote Similarity	NPD2625	Approved
0.6643	Remote Similarity	NPD2628	Approved
0.6643	Remote Similarity	NPD2159	Approved
0.6643	Remote Similarity	NPD2160	Approved
0.6643	Remote Similarity	NPD2627	Approved
0.6642	Remote Similarity	NPD2499	Approved
0.6642	Remote Similarity	NPD9568	Approved
0.6642	Remote Similarity	NPD2500	Approved
0.6642	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3524	Approved
0.6641	Remote Similarity	NPD3526	Approved
0.6621	Remote Similarity	NPD2606	Approved
0.6621	Remote Similarity	NPD3595	Approved
0.6621	Remote Similarity	NPD3594	Approved
0.6621	Remote Similarity	NPD2605	Approved
0.662	Remote Similarity	NPD6583	Phase 3
0.662	Remote Similarity	NPD6582	Phase 2
0.6619	Remote Similarity	NPD3049	Approved
0.6615	Remote Similarity	NPD10	Approved
0.6615	Remote Similarity	NPD314	Approved
0.6615	Remote Similarity	NPD309	Approved
0.6615	Remote Similarity	NPD315	Approved
0.6615	Remote Similarity	NPD311	Approved
0.6615	Remote Similarity	NPD310	Approved
0.6606	Remote Similarity	NPD2388	Discontinued
0.66	Remote Similarity	NPD1753	Discontinued
0.6599	Remote Similarity	NPD7715	Approved
0.6599	Remote Similarity	NPD7714	Approved
0.6599	Remote Similarity	NPD7477	Discontinued
0.6599	Remote Similarity	NPD5745	Approved
0.6597	Remote Similarity	NPD602	Approved
0.6597	Remote Similarity	NPD599	Approved
0.6597	Remote Similarity	NPD859	Approved
0.6597	Remote Similarity	NPD858	Approved
0.6596	Remote Similarity	NPD3974	Phase 2
0.6596	Remote Similarity	NPD4807	Approved
0.6596	Remote Similarity	NPD4806	Approved
0.6594	Remote Similarity	NPD828	Approved
0.6589	Remote Similarity	NPD4719	Phase 2
0.6587	Remote Similarity	NPD7177	Discontinued
0.6587	Remote Similarity	NPD844	Approved
0.6587	Remote Similarity	NPD2860	Approved
0.6587	Remote Similarity	NPD2859	Approved
0.6585	Remote Similarity	NPD7484	Phase 3
0.6585	Remote Similarity	NPD7485	Phase 3
0.6582	Remote Similarity	NPD824	Approved
0.6579	Remote Similarity	NPD4257	Approved
0.6579	Remote Similarity	NPD4256	Phase 2
0.6577	Remote Similarity	NPD3052	Approved
0.6577	Remote Similarity	NPD3054	Approved
0.6575	Remote Similarity	NPD5163	Phase 2
0.6575	Remote Similarity	NPD5156	Approved
0.6575	Remote Similarity	NPD5155	Approved
0.6573	Remote Similarity	NPD5311	Approved
0.6573	Remote Similarity	NPD3125	Approved

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