NPASS Compound

Structure

CID246076 OpenBabel06191716042D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.8370 3.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2410 1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9297 -0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8318 -0.7792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2560 3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5068 2.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6923 2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2371 2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2946 0.9705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9183 -0.3725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4769 1.5461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6978 2.1115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9002 1.0288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2910 1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3232 0.9463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9999 0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1093 -0.9603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5997 -0.7852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 0.6220 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 8 2 0 0 0 0 2 9 2 0 0 0 0 3 10 2 0 0 0 0 4 11 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 6 1 1 0 0 0 12 16 1 0 0 0 0 13 7 1 1 0 0 0 13 15 1 0 0 0 0 14 20 1 1 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 16 21 1 6 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.14
Volume:	298.897
LogP:	2.113
LogD:	2.373
LogS:	-3.329
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.572
Fsp3:	0.529
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:	-4.685
MDCK Permeability:	0.0001300037110922858
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.233

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.798
Plasma Protein Binding (PPB):	62.473045349121094%
Volume Distribution (VD):	1.458
Pgp-substrate:	45.757442474365234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.462
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.263
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	7.767
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.865
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.259
Carcinogencity:	0.405
Eye Corrosion:	0.819
Eye Irritation:	0.513
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC246076

Natural Product ID:	NPC246076
*Common Name:**	3Beta-Acetoxyguaia-4(15),10(14),11(13)-Trien-12,6Alpha-Olide
IUPAC Name:	[(3aS,6aR,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] acetate
Synonyms:
Standard InCHIKey:	GKMFOEIZCLMZDE-QXKUPLGCSA-N
Standard InCHI:	InChI=1S/C17H20O4/c1-8-5-6-12-9(2)17(19)21-16(12)15-10(3)14(7-13(8)15)20-11(4)18/h12-16H,1-3,5-7H2,4H3/t12-,13-,14-,15-,16-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2[C@H](C1=C)[C@H]1OC(=O)C(=C)[C@@H]1CCC2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL371402
PubChem CID:	12445012
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:0001770] Guaianolides 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
NPO8355	Zaluzania triloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)97900-1]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1080/10412905.2001.9699624]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11912066]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12419922]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21188975]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33264011]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8355	Zaluzania triloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29515	Laurus nobilis	Species	Lauraceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	100.0	uM	PMID[564335]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-2.0	n.a.	PMID[564335]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	100.0	uM	PMID[564336]

☑ 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 NPC246076 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	246
0.1-0.2	1956
0.2-0.3	7472
0.3-0.4	15886
0.4-0.5	8936
0.5-0.6	6054
0.6-0.7	1688
0.7-0.8	316
0.8-0.85	76
0.85-0.9	51
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC64153
0.95	High Similarity	NPC304558
0.9383	High Similarity	NPC24728
0.9268	High Similarity	NPC217983
0.9268	High Similarity	NPC207114
0.9268	High Similarity	NPC471149
0.9157	High Similarity	NPC472872
0.9157	High Similarity	NPC283409
0.9048	High Similarity	NPC54065
0.9048	High Similarity	NPC297474
0.9048	High Similarity	NPC19087
0.9036	High Similarity	NPC79549
0.9024	High Similarity	NPC187661
0.9012	High Similarity	NPC224386
0.9012	High Similarity	NPC194859
0.8947	High Similarity	NPC320537
0.8947	High Similarity	NPC143979
0.8941	High Similarity	NPC171360
0.8941	High Similarity	NPC63193
0.8941	High Similarity	NPC293001
0.8941	High Similarity	NPC57304
0.8941	High Similarity	NPC286341
0.8941	High Similarity	NPC133888
0.8941	High Similarity	NPC191339
0.8941	High Similarity	NPC29821
0.8941	High Similarity	NPC184063
0.8941	High Similarity	NPC35959
0.8929	High Similarity	NPC38392
0.8929	High Similarity	NPC155935
0.8929	High Similarity	NPC215556
0.8916	High Similarity	NPC118601
0.8916	High Similarity	NPC270270
0.8902	High Similarity	NPC284534
0.8902	High Similarity	NPC300082
0.8902	High Similarity	NPC235792
0.8902	High Similarity	NPC204105
0.8889	High Similarity	NPC54468
0.8824	High Similarity	NPC216284
0.8824	High Similarity	NPC35809
0.881	High Similarity	NPC178875
0.8795	High Similarity	NPC56593
0.8721	High Similarity	NPC155215
0.8721	High Similarity	NPC475925
0.8659	High Similarity	NPC128246
0.8642	High Similarity	NPC126248
0.8642	High Similarity	NPC47635
0.8636	High Similarity	NPC476053
0.8636	High Similarity	NPC472873
0.8636	High Similarity	NPC163228
0.8636	High Similarity	NPC167893
0.8621	High Similarity	NPC258216
0.8621	High Similarity	NPC472874
0.8608	High Similarity	NPC208223
0.8588	High Similarity	NPC224652
0.8571	High Similarity	NPC238593
0.8539	High Similarity	NPC91771
0.8539	High Similarity	NPC24956
0.8539	High Similarity	NPC142529
0.8539	High Similarity	NPC18019
0.8523	High Similarity	NPC198853
0.8523	High Similarity	NPC473331
0.8523	High Similarity	NPC127019
0.8519	High Similarity	NPC6823
0.8519	High Similarity	NPC293418
0.8519	High Similarity	NPC290508
0.8519	High Similarity	NPC73052
0.8506	High Similarity	NPC133698
0.8488	Intermediate Similarity	NPC4986
0.8444	Intermediate Similarity	NPC474313
0.8444	Intermediate Similarity	NPC471150
0.8434	Intermediate Similarity	NPC245665
0.8434	Intermediate Similarity	NPC111409
0.8427	Intermediate Similarity	NPC67584
0.8427	Intermediate Similarity	NPC213698
0.8421	Intermediate Similarity	NPC5714
0.8409	Intermediate Similarity	NPC200237
0.8409	Intermediate Similarity	NPC153590
0.8409	Intermediate Similarity	NPC308656
0.8409	Intermediate Similarity	NPC60386
0.8409	Intermediate Similarity	NPC473263
0.8409	Intermediate Similarity	NPC473234
0.8409	Intermediate Similarity	NPC473273
0.8395	Intermediate Similarity	NPC182550
0.8372	Intermediate Similarity	NPC91248
0.8353	Intermediate Similarity	NPC470242
0.8353	Intermediate Similarity	NPC67493
0.8353	Intermediate Similarity	NPC236692
0.8353	Intermediate Similarity	NPC309757
0.8333	Intermediate Similarity	NPC213078
0.8315	Intermediate Similarity	NPC470010
0.8315	Intermediate Similarity	NPC262133
0.8315	Intermediate Similarity	NPC470013
0.8315	Intermediate Similarity	NPC323008
0.8315	Intermediate Similarity	NPC477131
0.8295	Intermediate Similarity	NPC131209
0.8293	Intermediate Similarity	NPC276356
0.8293	Intermediate Similarity	NPC156658
0.8293	Intermediate Similarity	NPC74673
0.8293	Intermediate Similarity	NPC258965
0.8293	Intermediate Similarity	NPC69271
0.8261	Intermediate Similarity	NPC186861
0.8242	Intermediate Similarity	NPC311904
0.8242	Intermediate Similarity	NPC161493
0.8222	Intermediate Similarity	NPC52044
0.8222	Intermediate Similarity	NPC170120
0.8222	Intermediate Similarity	NPC224689
0.8214	Intermediate Similarity	NPC128429
0.8202	Intermediate Similarity	NPC135776
0.8182	Intermediate Similarity	NPC37607
0.8182	Intermediate Similarity	NPC301969
0.8172	Intermediate Similarity	NPC171759
0.8152	Intermediate Similarity	NPC45125
0.8152	Intermediate Similarity	NPC49833
0.8152	Intermediate Similarity	NPC249171
0.8148	Intermediate Similarity	NPC470240
0.8148	Intermediate Similarity	NPC476794
0.814	Intermediate Similarity	NPC107787
0.814	Intermediate Similarity	NPC162071
0.8118	Intermediate Similarity	NPC115786
0.8072	Intermediate Similarity	NPC474981
0.8068	Intermediate Similarity	NPC168679
0.8068	Intermediate Similarity	NPC12872
0.8065	Intermediate Similarity	NPC471381
0.8046	Intermediate Similarity	NPC201658
0.8046	Intermediate Similarity	NPC190753
0.8046	Intermediate Similarity	NPC186148
0.8043	Intermediate Similarity	NPC304445
0.8043	Intermediate Similarity	NPC181151
0.8043	Intermediate Similarity	NPC170143
0.8043	Intermediate Similarity	NPC108475
0.8043	Intermediate Similarity	NPC236580
0.8043	Intermediate Similarity	NPC213947
0.8023	Intermediate Similarity	NPC78089
0.8022	Intermediate Similarity	NPC304886
0.8	Intermediate Similarity	NPC474472
0.8	Intermediate Similarity	NPC473148
0.8	Intermediate Similarity	NPC272814
0.8	Intermediate Similarity	NPC257358
0.8	Intermediate Similarity	NPC475788
0.8	Intermediate Similarity	NPC318468
0.7979	Intermediate Similarity	NPC150923
0.7978	Intermediate Similarity	NPC62815
0.7976	Intermediate Similarity	NPC281949
0.7976	Intermediate Similarity	NPC301477
0.7976	Intermediate Similarity	NPC25684
0.7957	Intermediate Similarity	NPC221615
0.7955	Intermediate Similarity	NPC177629
0.7955	Intermediate Similarity	NPC58219
0.7931	Intermediate Similarity	NPC284902
0.7931	Intermediate Similarity	NPC50637
0.7907	Intermediate Similarity	NPC138647
0.7907	Intermediate Similarity	NPC156485
0.7907	Intermediate Similarity	NPC470238
0.7901	Intermediate Similarity	NPC471491
0.7895	Intermediate Similarity	NPC80144
0.7889	Intermediate Similarity	NPC221282
0.7865	Intermediate Similarity	NPC92974
0.7865	Intermediate Similarity	NPC32922
0.7857	Intermediate Similarity	NPC51507
0.7857	Intermediate Similarity	NPC302426
0.7841	Intermediate Similarity	NPC231889
0.7841	Intermediate Similarity	NPC475703
0.7841	Intermediate Similarity	NPC175293
0.7841	Intermediate Similarity	NPC5130
0.7835	Intermediate Similarity	NPC54737
0.7835	Intermediate Similarity	NPC44004
0.7826	Intermediate Similarity	NPC475900
0.7816	Intermediate Similarity	NPC215364
0.7791	Intermediate Similarity	NPC215294
0.7791	Intermediate Similarity	NPC39588
0.7789	Intermediate Similarity	NPC67296
0.7778	Intermediate Similarity	NPC474323
0.7778	Intermediate Similarity	NPC206614
0.7778	Intermediate Similarity	NPC475776
0.7765	Intermediate Similarity	NPC39411
0.7765	Intermediate Similarity	NPC35089
0.7765	Intermediate Similarity	NPC10276
0.7765	Intermediate Similarity	NPC141810
0.7765	Intermediate Similarity	NPC255580
0.7753	Intermediate Similarity	NPC202672
0.7742	Intermediate Similarity	NPC474297
0.7742	Intermediate Similarity	NPC476009
0.7742	Intermediate Similarity	NPC126156
0.7738	Intermediate Similarity	NPC19841
0.7738	Intermediate Similarity	NPC617
0.7727	Intermediate Similarity	NPC475019
0.7727	Intermediate Similarity	NPC476015
0.7727	Intermediate Similarity	NPC474762
0.7727	Intermediate Similarity	NPC474949
0.7711	Intermediate Similarity	NPC65603
0.7708	Intermediate Similarity	NPC86077
0.7692	Intermediate Similarity	NPC123177
0.7692	Intermediate Similarity	NPC74103
0.7692	Intermediate Similarity	NPC12172
0.7692	Intermediate Similarity	NPC208886
0.7692	Intermediate Similarity	NPC290651
0.7692	Intermediate Similarity	NPC70595
0.7692	Intermediate Similarity	NPC150978
0.7684	Intermediate Similarity	NPC70865
0.7683	Intermediate Similarity	NPC138408

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 NPC246076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	2732
0.2-0.3	3962
0.3-0.4	1506
0.4-0.5	448
0.5-0.6	186
0.6-0.7	27
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8488	Intermediate Similarity	NPD1695	Approved
0.7576	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4249	Approved
0.6882	Remote Similarity	NPD4251	Approved
0.6882	Remote Similarity	NPD4250	Approved
0.6857	Remote Similarity	NPD6371	Approved
0.6848	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5785	Approved
0.6813	Remote Similarity	NPD5362	Discontinued
0.6796	Remote Similarity	NPD6008	Approved
0.6729	Remote Similarity	NPD6053	Discontinued
0.6703	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6593	Remote Similarity	NPD5369	Approved
0.6535	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD6435	Approved
0.6522	Remote Similarity	NPD4270	Approved
0.6522	Remote Similarity	NPD4269	Approved
0.6484	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD7640	Approved
0.6465	Remote Similarity	NPD5282	Discontinued
0.6458	Remote Similarity	NPD6903	Approved
0.6452	Remote Similarity	NPD7154	Phase 3
0.6421	Remote Similarity	NPD6684	Approved
0.6421	Remote Similarity	NPD7521	Approved
0.6421	Remote Similarity	NPD7334	Approved
0.6421	Remote Similarity	NPD6409	Approved
0.6421	Remote Similarity	NPD5330	Approved
0.6421	Remote Similarity	NPD7146	Approved
0.6421	Remote Similarity	NPD5786	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6327	Remote Similarity	NPD7838	Discovery
0.6304	Remote Similarity	NPD4252	Approved
0.6304	Remote Similarity	NPD5368	Approved
0.6304	Remote Similarity	NPD4820	Approved
0.6304	Remote Similarity	NPD4822	Approved
0.6304	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD4821	Approved
0.6289	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5331	Approved
0.6277	Remote Similarity	NPD5332	Approved
0.6264	Remote Similarity	NPD4271	Approved
0.6264	Remote Similarity	NPD4268	Approved
0.6263	Remote Similarity	NPD5693	Phase 1
0.6263	Remote Similarity	NPD8035	Phase 2
0.6263	Remote Similarity	NPD8034	Phase 2
0.6238	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4790	Discontinued
0.6204	Remote Similarity	NPD6686	Approved
0.617	Remote Similarity	NPD5209	Approved
0.6162	Remote Similarity	NPD5207	Approved
0.6122	Remote Similarity	NPD6672	Approved
0.6122	Remote Similarity	NPD5737	Approved
0.61	Remote Similarity	NPD7983	Approved
0.6087	Remote Similarity	NPD4802	Phase 2
0.6087	Remote Similarity	NPD4238	Approved
0.6087	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4225	Approved
0.6058	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5778	Approved
0.604	Remote Similarity	NPD5779	Approved
0.6038	Remote Similarity	NPD7632	Discontinued
0.6036	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6001	Approved
0.5976	Remote Similarity	NPD3198	Approved
0.5963	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD8039	Approved
0.5929	Remote Similarity	NPD8133	Approved
0.5922	Remote Similarity	NPD5695	Phase 3
0.5905	Remote Similarity	NPD5696	Approved
0.59	Remote Similarity	NPD6080	Approved
0.59	Remote Similarity	NPD6051	Approved
0.59	Remote Similarity	NPD6673	Approved
0.59	Remote Similarity	NPD6904	Approved
0.5849	Remote Similarity	NPD6648	Approved
0.5842	Remote Similarity	NPD5692	Phase 3
0.5825	Remote Similarity	NPD7900	Approved
0.5825	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6412	Phase 2
0.5818	Remote Similarity	NPD5697	Approved
0.5816	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6083	Phase 2
0.581	Remote Similarity	NPD6084	Phase 2
0.5804	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5208	Approved
0.5795	Remote Similarity	NPD229	Approved
0.5794	Remote Similarity	NPD5344	Discontinued
0.5789	Remote Similarity	NPD4632	Approved
0.5785	Remote Similarity	NPD7507	Approved
0.5784	Remote Similarity	NPD6050	Approved
0.5784	Remote Similarity	NPD5694	Approved
0.5784	Remote Similarity	NPD5281	Approved
0.5784	Remote Similarity	NPD5284	Approved
0.5784	Remote Similarity	NPD7637	Suspended
0.5778	Remote Similarity	NPD5777	Approved
0.5776	Remote Similarity	NPD7115	Discovery
0.5773	Remote Similarity	NPD4788	Approved
0.5766	Remote Similarity	NPD6881	Approved
0.5766	Remote Similarity	NPD7320	Approved
0.5766	Remote Similarity	NPD6899	Approved
0.5766	Remote Similarity	NPD6011	Approved
0.576	Remote Similarity	NPD6845	Suspended
0.5758	Remote Similarity	NPD6098	Approved
0.5752	Remote Similarity	NPD6650	Approved
0.5752	Remote Similarity	NPD6649	Approved
0.5743	Remote Similarity	NPD6101	Approved
0.5743	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6675	Approved
0.5727	Remote Similarity	NPD5739	Approved
0.5727	Remote Similarity	NPD7128	Approved
0.5727	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD3665	Phase 1
0.5714	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD3133	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD3666	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5702	Remote Similarity	NPD7492	Approved
0.5688	Remote Similarity	NPD6052	Approved
0.568	Remote Similarity	NPD7260	Phase 2
0.5676	Remote Similarity	NPD5701	Approved
0.567	Remote Similarity	NPD3667	Approved
0.5664	Remote Similarity	NPD7102	Approved
0.5664	Remote Similarity	NPD7290	Approved
0.5664	Remote Similarity	NPD6883	Approved
0.566	Remote Similarity	NPD7902	Approved
0.5656	Remote Similarity	NPD6616	Approved
0.5645	Remote Similarity	NPD7319	Approved
0.5641	Remote Similarity	NPD6009	Approved
0.5631	Remote Similarity	NPD6411	Approved
0.563	Remote Similarity	NPD6054	Approved
0.563	Remote Similarity	NPD6319	Approved
0.5625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8130	Phase 1
0.5614	Remote Similarity	NPD6869	Approved
0.5614	Remote Similarity	NPD6847	Approved
0.5614	Remote Similarity	NPD6617	Approved
0.561	Remote Similarity	NPD7078	Approved
0.56	Remote Similarity	NPD3618	Phase 1

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