NPASS Compound

Structure

CID131669 OpenBabel06191715492D 26 27 0 0 1 0 0 0 0 0999 V2000 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9095 0.6338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1174 1.6119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3267 -3.8052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3743 2.2811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.9209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 -3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 7 16 1 0 0 0 0 8 15 2 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 19 1 0 0 0 0 12 21 2 0 0 0 0 12 24 1 0 0 0 0 13 22 2 0 0 0 0 13 25 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 6 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 11 1 1 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.15
Volume:	365.78
LogP:	0.581
LogD:	1.238
LogS:	-2.383
# Rotatable Bonds:	6
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.35
Synthetic Accessibility Score:	4.668
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.879
MDCK Permeability:	0.00011911765614058822
Pgp-inhibitor:	0.073
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.943
20% Bioavailability (F20%):	0.659
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	60.696937561035156%
Volume Distribution (VD):	0.297
Pgp-substrate:	62.75251388549805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.175
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	3.108
Half-life (T1/2):	0.941

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.772
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.525
Rat Oral Acute Toxicity:	0.514
Maximum Recommended Daily Dose:	0.141
Skin Sensitization:	0.628
Carcinogencity:	0.256
Eye Corrosion:	0.014
Eye Irritation:	0.06
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC131669

Natural Product ID:	NPC131669
*Common Name:**	(6S,7R,8S)-8,15-Diacetoxy-14-Hydroxymelampa-1(10),4,11(13)-Trien-12,6-Olide
IUPAC Name:	[(3aR,4S,6E,10Z,11aR)-4-acetyloxy-6-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-10-yl]methyl acetate
Synonyms:
Standard InCHIKey:	XFZPJBLGAHKFAT-KJYAUEFBSA-N
Standard InCHI:	InChI=1S/C19H24O7/c1-11-18-16(25-13(3)22)7-14(9-20)5-4-6-15(10-24-12(2)21)8-17(18)26-19(11)23/h5,8,16-18,20H,1,4,6-7,9-10H2,2-3H3/b14-5+,15-8-/t16-,17+,18+/m0/s1
SMILES:	C=C1[C@@H]2[C@H](C/C(=CCC/C(=C/[C@H]2OC1=O)/COC(=O)C)/CO)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481634
PubChem CID:	10406449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO25689	Mikania minima	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10757707]
NPO23784	Botryosphaeria rhodina	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432876]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[300080]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[300080]
NPO429	Chrysosporium merdarium	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9207909]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25689	Mikania minima	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23784	Botryosphaeria rhodina	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9890	Pleurobranchus membranaceus	Species	Pleurobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO429	Chrysosporium merdarium	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7685	Ormosia indurata	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO533	Heterophragma adenophyllum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5671	Streptomyces davawensis	Species	Streptomycetaceae	Bacteria	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	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	2700.0	nM	PMID[519909]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5500.0	nM	PMID[519909]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	6500.0	nM	PMID[519909]

☑ 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 NPC131669 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	169
0.1-0.2	1149
0.2-0.3	4885
0.3-0.4	12774
0.4-0.5	11947
0.5-0.6	6912
0.6-0.7	3662
0.7-0.8	970
0.8-0.85	91
0.85-0.9	67
0.9-0.95	48
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473390
0.987	High Similarity	NPC229825
0.9747	High Similarity	NPC255307
0.9744	High Similarity	NPC169575
0.9744	High Similarity	NPC40746
0.974	High Similarity	NPC24417
0.9625	High Similarity	NPC305475
0.9625	High Similarity	NPC475461
0.962	High Similarity	NPC476804
0.962	High Similarity	NPC191476
0.962	High Similarity	NPC158756
0.962	High Similarity	NPC114979
0.95	High Similarity	NPC470755
0.9481	High Similarity	NPC98557
0.9481	High Similarity	NPC167881
0.9383	High Similarity	NPC469910
0.9375	High Similarity	NPC96259
0.9375	High Similarity	NPC141193
0.9351	High Similarity	NPC196653
0.9351	High Similarity	NPC471465
0.925	High Similarity	NPC59097
0.9241	High Similarity	NPC52861
0.9221	High Similarity	NPC476028
0.9221	High Similarity	NPC7563
0.9221	High Similarity	NPC141789
0.9221	High Similarity	NPC171204
0.9221	High Similarity	NPC116177
0.9221	High Similarity	NPC320630
0.9167	High Similarity	NPC469368
0.9167	High Similarity	NPC475855
0.9157	High Similarity	NPC476803
0.9157	High Similarity	NPC475819
0.9157	High Similarity	NPC476805
0.9146	High Similarity	NPC150755
0.9103	High Similarity	NPC108816
0.9103	High Similarity	NPC93763
0.9091	High Similarity	NPC68819
0.9024	High Similarity	NPC165162
0.9012	High Similarity	NPC116543
0.8987	High Similarity	NPC270126
0.8953	High Similarity	NPC475838
0.8953	High Similarity	NPC125674
0.8953	High Similarity	NPC228451
0.8941	High Similarity	NPC179394
0.8941	High Similarity	NPC474232
0.8941	High Similarity	NPC144133
0.8929	High Similarity	NPC473715
0.8875	High Similarity	NPC281132
0.8861	High Similarity	NPC267231
0.8851	High Similarity	NPC474247
0.8837	High Similarity	NPC473321
0.875	High Similarity	NPC89128
0.875	High Similarity	NPC471142
0.8736	High Similarity	NPC295204
0.8736	High Similarity	NPC162205
0.8736	High Similarity	NPC475302
0.8736	High Similarity	NPC273579
0.8736	High Similarity	NPC288240
0.8734	High Similarity	NPC97516
0.8721	High Similarity	NPC473619
0.8701	High Similarity	NPC269206
0.8701	High Similarity	NPC295633
0.8701	High Similarity	NPC58956
0.8659	High Similarity	NPC89555
0.8652	High Similarity	NPC279621
0.8652	High Similarity	NPC230800
0.8608	High Similarity	NPC235906
0.8605	High Similarity	NPC474032
0.8605	High Similarity	NPC218927
0.8605	High Similarity	NPC206001
0.859	High Similarity	NPC476355
0.859	High Similarity	NPC140287
0.8571	High Similarity	NPC163003
0.8571	High Similarity	NPC21469
0.8554	High Similarity	NPC250315
0.8539	High Similarity	NPC477922
0.8537	High Similarity	NPC25684
0.8537	High Similarity	NPC281949
0.8537	High Similarity	NPC301477
0.8537	High Similarity	NPC141810
0.8523	High Similarity	NPC475912
0.8519	High Similarity	NPC470244
0.8519	High Similarity	NPC470239
0.8506	High Similarity	NPC129419
0.8488	Intermediate Similarity	NPC477302
0.8488	Intermediate Similarity	NPC136879
0.8471	Intermediate Similarity	NPC50637
0.8444	Intermediate Similarity	NPC477921
0.8427	Intermediate Similarity	NPC303942
0.8427	Intermediate Similarity	NPC57405
0.8391	Intermediate Similarity	NPC295312
0.8391	Intermediate Similarity	NPC268298
0.8375	Intermediate Similarity	NPC123360
0.8372	Intermediate Similarity	NPC160138
0.837	Intermediate Similarity	NPC288876
0.8354	Intermediate Similarity	NPC114727
0.8354	Intermediate Similarity	NPC476590
0.8353	Intermediate Similarity	NPC261380
0.8333	Intermediate Similarity	NPC36954
0.8333	Intermediate Similarity	NPC474703
0.8333	Intermediate Similarity	NPC270013
0.8333	Intermediate Similarity	NPC14961
0.8333	Intermediate Similarity	NPC304886
0.8333	Intermediate Similarity	NPC471141
0.8315	Intermediate Similarity	NPC469692
0.8315	Intermediate Similarity	NPC469645
0.8313	Intermediate Similarity	NPC470241
0.8313	Intermediate Similarity	NPC325031
0.8293	Intermediate Similarity	NPC617
0.8276	Intermediate Similarity	NPC202672
0.8272	Intermediate Similarity	NPC474760
0.8272	Intermediate Similarity	NPC476794
0.8272	Intermediate Similarity	NPC470240
0.8261	Intermediate Similarity	NPC471144
0.825	Intermediate Similarity	NPC155587
0.8242	Intermediate Similarity	NPC306041
0.8242	Intermediate Similarity	NPC476315
0.8242	Intermediate Similarity	NPC473859
0.8222	Intermediate Similarity	NPC81386
0.8222	Intermediate Similarity	NPC474035
0.8222	Intermediate Similarity	NPC121825
0.8222	Intermediate Similarity	NPC474338
0.8214	Intermediate Similarity	NPC474252
0.8202	Intermediate Similarity	NPC184463
0.8202	Intermediate Similarity	NPC30515
0.8182	Intermediate Similarity	NPC166919
0.8161	Intermediate Similarity	NPC266957
0.8132	Intermediate Similarity	NPC475659
0.8125	Intermediate Similarity	NPC48641
0.8111	Intermediate Similarity	NPC476300
0.8111	Intermediate Similarity	NPC81419
0.8111	Intermediate Similarity	NPC179746
0.8111	Intermediate Similarity	NPC212486
0.8101	Intermediate Similarity	NPC129665
0.809	Intermediate Similarity	NPC51004
0.809	Intermediate Similarity	NPC473448
0.809	Intermediate Similarity	NPC476004
0.809	Intermediate Similarity	NPC474761
0.8072	Intermediate Similarity	NPC475210
0.8072	Intermediate Similarity	NPC178277
0.8072	Intermediate Similarity	NPC19841
0.8068	Intermediate Similarity	NPC287089
0.8065	Intermediate Similarity	NPC141191
0.8065	Intermediate Similarity	NPC187268
0.8065	Intermediate Similarity	NPC473326
0.8052	Intermediate Similarity	NPC194871
0.8049	Intermediate Similarity	NPC65603
0.8046	Intermediate Similarity	NPC107787
0.8046	Intermediate Similarity	NPC261721
0.8046	Intermediate Similarity	NPC469483
0.8023	Intermediate Similarity	NPC159635
0.8023	Intermediate Similarity	NPC115786
0.8023	Intermediate Similarity	NPC295799
0.8023	Intermediate Similarity	NPC82297
0.8022	Intermediate Similarity	NPC262133
0.8022	Intermediate Similarity	NPC198853
0.8022	Intermediate Similarity	NPC470013
0.8022	Intermediate Similarity	NPC470010
0.8022	Intermediate Similarity	NPC477131
0.8022	Intermediate Similarity	NPC323008
0.8	Intermediate Similarity	NPC85772
0.8	Intermediate Similarity	NPC131209
0.8	Intermediate Similarity	NPC300312
0.8	Intermediate Similarity	NPC12172
0.8	Intermediate Similarity	NPC208886
0.8	Intermediate Similarity	NPC475925
0.8	Intermediate Similarity	NPC261607
0.8	Intermediate Similarity	NPC471148
0.8	Intermediate Similarity	NPC133698
0.8	Intermediate Similarity	NPC111114
0.7979	Intermediate Similarity	NPC475949
0.7978	Intermediate Similarity	NPC307411
0.7978	Intermediate Similarity	NPC151770
0.7975	Intermediate Similarity	NPC67183
0.7957	Intermediate Similarity	NPC169205
0.7957	Intermediate Similarity	NPC471462
0.7957	Intermediate Similarity	NPC161493
0.7955	Intermediate Similarity	NPC237540
0.7935	Intermediate Similarity	NPC213698
0.7935	Intermediate Similarity	NPC67584
0.7935	Intermediate Similarity	NPC52044
0.7935	Intermediate Similarity	NPC170120
0.7931	Intermediate Similarity	NPC78089
0.7931	Intermediate Similarity	NPC215364
0.7895	Intermediate Similarity	NPC150923
0.7895	Intermediate Similarity	NPC474339
0.7895	Intermediate Similarity	NPC185141
0.7895	Intermediate Similarity	NPC164598
0.7895	Intermediate Similarity	NPC46998
0.7895	Intermediate Similarity	NPC133907
0.7895	Intermediate Similarity	NPC473332
0.7895	Intermediate Similarity	NPC110443
0.7895	Intermediate Similarity	NPC128733
0.7882	Intermediate Similarity	NPC471325
0.7872	Intermediate Similarity	NPC474213
0.7865	Intermediate Similarity	NPC207114
0.7865	Intermediate Similarity	NPC260343
0.7865	Intermediate Similarity	NPC217983
0.7849	Intermediate Similarity	NPC185553
0.7849	Intermediate Similarity	NPC213078

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 NPC131669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1723
0.2-0.3	3732
0.3-0.4	2427
0.4-0.5	701
0.5-0.6	336
0.6-0.7	54
0.7-0.8	25
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
0.7742	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7154	Phase 3
0.7558	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5785	Approved
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.7333	Intermediate Similarity	NPD5363	Approved
0.7326	Intermediate Similarity	NPD4268	Approved
0.7326	Intermediate Similarity	NPD4271	Approved
0.732	Intermediate Similarity	NPD4225	Approved
0.7303	Intermediate Similarity	NPD5362	Discontinued
0.7253	Intermediate Similarity	NPD4249	Approved
0.7204	Intermediate Similarity	NPD1695	Approved
0.7191	Intermediate Similarity	NPD4269	Approved
0.7191	Intermediate Similarity	NPD4270	Approved
0.7174	Intermediate Similarity	NPD4251	Approved
0.7174	Intermediate Similarity	NPD4250	Approved
0.7159	Intermediate Similarity	NPD4821	Approved
0.7159	Intermediate Similarity	NPD4820	Approved
0.7159	Intermediate Similarity	NPD4822	Approved
0.7159	Intermediate Similarity	NPD4819	Approved
0.7159	Intermediate Similarity	NPD4252	Approved
0.7157	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7838	Discovery
0.7115	Intermediate Similarity	NPD6371	Approved
0.7065	Intermediate Similarity	NPD5786	Approved
0.7053	Intermediate Similarity	NPD7983	Approved
0.7	Intermediate Similarity	NPD6435	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5778	Approved
0.6979	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD1694	Approved
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5369	Approved
0.6887	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5368	Approved
0.6762	Remote Similarity	NPD6686	Approved
0.6739	Remote Similarity	NPD5332	Approved
0.6739	Remote Similarity	NPD5331	Approved
0.6703	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5370	Suspended
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6399	Phase 3
0.663	Remote Similarity	NPD5209	Approved
0.6629	Remote Similarity	NPD4756	Discovery
0.66	Remote Similarity	NPD7839	Suspended
0.6577	Remote Similarity	NPD7115	Discovery
0.6569	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD7640	Approved
0.6566	Remote Similarity	NPD5282	Discontinued
0.6531	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6411	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.6506	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5344	Discontinued
0.6471	Remote Similarity	NPD7638	Approved
0.642	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8039	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.6353	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6648	Approved
0.6214	Remote Similarity	NPD6083	Phase 2
0.6214	Remote Similarity	NPD6084	Phase 2
0.6214	Remote Similarity	NPD7902	Approved
0.6207	Remote Similarity	NPD8517	Approved
0.6207	Remote Similarity	NPD8516	Approved
0.6207	Remote Similarity	NPD8515	Approved
0.6207	Remote Similarity	NPD8513	Phase 3
0.6204	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD3197	Phase 1
0.6186	Remote Similarity	NPD6422	Discontinued
0.6176	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD5696	Approved
0.6147	Remote Similarity	NPD6899	Approved
0.6147	Remote Similarity	NPD6881	Approved
0.6126	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD7128	Approved
0.6111	Remote Similarity	NPD5739	Approved
0.6111	Remote Similarity	NPD6402	Approved
0.6105	Remote Similarity	NPD3667	Approved
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6372	Approved
0.6091	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6013	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6078	Remote Similarity	NPD7748	Approved
0.6075	Remote Similarity	NPD6647	Phase 2
0.6055	Remote Similarity	NPD5701	Approved
0.6042	Remote Similarity	NPD6110	Phase 1
0.604	Remote Similarity	NPD7515	Phase 2
0.6036	Remote Similarity	NPD7102	Approved
0.6036	Remote Similarity	NPD6883	Approved
0.6036	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7290	Approved
0.602	Remote Similarity	NPD7334	Approved
0.602	Remote Similarity	NPD5330	Approved
0.602	Remote Similarity	NPD6409	Approved
0.602	Remote Similarity	NPD3618	Phase 1
0.602	Remote Similarity	NPD7521	Approved
0.602	Remote Similarity	NPD7146	Approved
0.602	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD342	Phase 1
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD7320	Approved
0.5982	Remote Similarity	NPD8130	Phase 1
0.5982	Remote Similarity	NPD6869	Approved
0.5982	Remote Similarity	NPD6847	Approved
0.5982	Remote Similarity	NPD6617	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.5981	Remote Similarity	NPD7632	Discontinued
0.5979	Remote Similarity	NPD4786	Approved
0.5979	Remote Similarity	NPD3133	Approved
0.5979	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD3666	Approved
0.5979	Remote Similarity	NPD3665	Phase 1
0.5962	Remote Similarity	NPD4228	Discovery
0.5962	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD368	Approved
0.595	Remote Similarity	NPD8074	Phase 3
0.5949	Remote Similarity	NPD3172	Approved
0.5929	Remote Similarity	NPD8297	Approved
0.5929	Remote Similarity	NPD6882	Approved
0.5922	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7900	Approved
0.59	Remote Similarity	NPD5737	Approved
0.59	Remote Similarity	NPD6672	Approved
0.59	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6903	Approved
0.5897	Remote Similarity	NPD6927	Phase 3
0.5895	Remote Similarity	NPD4695	Discontinued
0.5893	Remote Similarity	NPD6421	Discontinued
0.5882	Remote Similarity	NPD8035	Phase 2
0.5882	Remote Similarity	NPD5693	Phase 1
0.5882	Remote Similarity	NPD8034	Phase 2
0.5882	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5281	Approved
0.5882	Remote Similarity	NPD5284	Approved
0.5876	Remote Similarity	NPD6695	Phase 3
0.5875	Remote Similarity	NPD3195	Phase 2
0.5875	Remote Similarity	NPD4266	Approved
0.5875	Remote Similarity	NPD3196	Approved
0.5875	Remote Similarity	NPD3194	Approved
0.5872	Remote Similarity	NPD5141	Approved
0.5865	Remote Similarity	NPD5210	Approved
0.5865	Remote Similarity	NPD4629	Approved
0.5862	Remote Similarity	NPD3704	Approved
0.5862	Remote Similarity	NPD7331	Phase 2
0.5859	Remote Similarity	NPD5279	Phase 3
0.5842	Remote Similarity	NPD4753	Phase 2
0.5841	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD2204	Approved
0.5825	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6008	Approved
0.5794	Remote Similarity	NPD5286	Approved
0.5794	Remote Similarity	NPD4696	Approved
0.5794	Remote Similarity	NPD5285	Approved
0.578	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6274	Approved
0.5766	Remote Similarity	NPD6412	Phase 2
0.5766	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4755	Approved
0.5752	Remote Similarity	NPD2067	Discontinued
0.5752	Remote Similarity	NPD6420	Discontinued
0.5747	Remote Similarity	NPD7341	Phase 2
0.5738	Remote Similarity	NPD7507	Approved
0.5738	Remote Similarity	NPD8273	Phase 1
0.5728	Remote Similarity	NPD6079	Approved
0.5726	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7642	Approved
0.5702	Remote Similarity	NPD7830	Approved
0.5702	Remote Similarity	NPD7829	Approved
0.57	Remote Similarity	NPD4519	Discontinued
0.57	Remote Similarity	NPD4623	Approved
0.5688	Remote Similarity	NPD5226	Approved
0.5688	Remote Similarity	NPD4633	Approved
0.5688	Remote Similarity	NPD5225	Approved
0.5688	Remote Similarity	NPD5224	Approved
0.5686	Remote Similarity	NPD6051	Approved
0.5686	Remote Similarity	NPD5328	Approved
0.5684	Remote Similarity	NPD3732	Approved
0.5678	Remote Similarity	NPD7641	Discontinued
0.5673	Remote Similarity	NPD4202	Approved
0.5667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6413	Approved
0.566	Remote Similarity	NPD5221	Approved
0.566	Remote Similarity	NPD4697	Phase 3
0.566	Remote Similarity	NPD5222	Approved
0.566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7966	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