NPASS Compound

Structure

NPC469583 OpenBabel07101719132D 36 37 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 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 -3.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -4.8660 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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 3 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 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 10 1 0 0 0 0 2 11 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 2 0 0 0 0 6 17 1 0 0 0 0 7 26 1 0 0 0 0 8 26 1 0 0 0 0 10 14 2 0 0 0 0 11 15 2 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 17 28 2 0 0 0 0 17 33 1 0 0 0 0 18 16 1 1 0 0 0 18 22 1 0 0 0 0 19 34 1 0 0 0 0 20 26 1 0 0 0 0 20 29 1 0 0 0 0 21 27 1 6 0 0 0 21 36 1 0 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 27 1 0 0 0 0 23 35 1 0 0 0 0 24 30 2 0 0 0 0 24 34 1 0 0 0 0 25 31 2 0 0 0 0 25 35 1 0 0 0 0 26 32 1 0 0 0 0 27 9 1 6 0 0 0 27 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.27
Volume:	521.728
LogP:	2.223
LogD:	1.02
LogS:	-2.746
# Rotatable Bonds:	13
TPSA:	131.89
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.15
Synthetic Accessibility Score:	5.16
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
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:	-4.787
MDCK Permeability:	4.9936668801819906e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.519
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	68.31407928466797%
Volume Distribution (VD):	1.966
Pgp-substrate:	15.976396560668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.565
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.102
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.425

ADMET: Excretion

Clearance (CL):	6.757
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.988
Drug-inuced Liver Injury (DILI):	0.74
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.247
Skin Sensitization:	0.108
Carcinogencity:	0.031
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC469583

Natural Product ID:	NPC469583
*Common Name:**	1Beta-Acetoxy-1Beta,8-Diangloyloxy-10,11-Dihydroxy-3,4-Epoxybisabol-7(14)-Ene
IUPAC Name:	[(1R,3R,4S,6R)-4-acetyloxy-3-[5,6-dihydroxy-6-methyl-3-[(Z)-2-methylbut-2-enoyl]oxyhept-1-en-2-yl]-6-methyl-7-oxabicyclo[4.1.0]heptan-5-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	XVXHJNWLSXMTBN-CABOIKOWSA-N
Standard InCHI:	InChI=1S/C27H40O9/c1-10-14(3)24(30)34-19(13-20(29)26(7,8)32)16(5)18-12-21-27(9,36-21)23(22(18)33-17(6)28)35-25(31)15(4)11-2/h10-11,18-23,29,32H,5,12-13H2,1-4,6-9H3/b14-10-,15-11-/t18-,19?,20?,21-,22+,23?,27-/m1/s1
SMILES:	C/C=C(C(=O)OC(C(=C)[C@H]1C[C@H]2O[C@]2(C([C@H]1OC(=O)C)OC(=O)/C(=CC)/C)C)CC(C(O)(C)C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088331
PubChem CID:	46881271
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20073490]
NPO12711	Ligularia altaica	Species	Asteraceae	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
EC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[496505]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[496505]
NPT91	Cell Line	KB	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[496505]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	20.0	ug.mL-1	PMID[496505]

☑ 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 NPC469583 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	213
0.1-0.2	1577
0.2-0.3	4686
0.3-0.4	8242
0.4-0.5	15079
0.5-0.6	8355
0.6-0.7	3889
0.7-0.8	618
0.8-0.85	22
0.85-0.9	6
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC472996
0.9888	High Similarity	NPC472997
0.9778	High Similarity	NPC472998
0.9451	High Similarity	NPC472995
0.8778	High Similarity	NPC475087
0.8384	Intermediate Similarity	NPC472552
0.8384	Intermediate Similarity	NPC470972
0.8333	Intermediate Similarity	NPC181994
0.8317	Intermediate Similarity	NPC470980
0.8283	Intermediate Similarity	NPC472554
0.8252	Intermediate Similarity	NPC475586
0.82	Intermediate Similarity	NPC475038
0.82	Intermediate Similarity	NPC109195
0.8182	Intermediate Similarity	NPC79303
0.8182	Intermediate Similarity	NPC272223
0.8113	Intermediate Similarity	NPC477126
0.8105	Intermediate Similarity	NPC3952
0.8058	Intermediate Similarity	NPC474716
0.8058	Intermediate Similarity	NPC469558
0.8021	Intermediate Similarity	NPC122057
0.8021	Intermediate Similarity	NPC91251
0.8	Intermediate Similarity	NPC38855
0.8	Intermediate Similarity	NPC271295
0.7981	Intermediate Similarity	NPC475263
0.798	Intermediate Similarity	NPC199099
0.7941	Intermediate Similarity	NPC61442
0.7941	Intermediate Similarity	NPC23584
0.7921	Intermediate Similarity	NPC11974
0.7917	Intermediate Similarity	NPC177668
0.7885	Intermediate Similarity	NPC471205
0.7885	Intermediate Similarity	NPC473586
0.7879	Intermediate Similarity	NPC475380
0.7879	Intermediate Similarity	NPC209297
0.7843	Intermediate Similarity	NPC11956
0.7841	Intermediate Similarity	NPC477306
0.7835	Intermediate Similarity	NPC158061
0.783	Intermediate Similarity	NPC177047
0.7822	Intermediate Similarity	NPC188968
0.7818	Intermediate Similarity	NPC146280
0.7818	Intermediate Similarity	NPC124676
0.7812	Intermediate Similarity	NPC133450
0.7812	Intermediate Similarity	NPC161560
0.781	Intermediate Similarity	NPC469916
0.781	Intermediate Similarity	NPC472439
0.78	Intermediate Similarity	NPC473244
0.78	Intermediate Similarity	NPC205143
0.78	Intermediate Similarity	NPC475446
0.78	Intermediate Similarity	NPC311241
0.7798	Intermediate Similarity	NPC154363
0.7798	Intermediate Similarity	NPC234858
0.7798	Intermediate Similarity	NPC471127
0.7788	Intermediate Similarity	NPC473802
0.7788	Intermediate Similarity	NPC88349
0.7788	Intermediate Similarity	NPC51719
0.7778	Intermediate Similarity	NPC477314
0.7778	Intermediate Similarity	NPC276110
0.7767	Intermediate Similarity	NPC474822
0.7757	Intermediate Similarity	NPC470076
0.7755	Intermediate Similarity	NPC472196
0.7755	Intermediate Similarity	NPC238090
0.7755	Intermediate Similarity	NPC472195
0.7748	Intermediate Similarity	NPC472667
0.7742	Intermediate Similarity	NPC231601
0.7732	Intermediate Similarity	NPC471378
0.7732	Intermediate Similarity	NPC312471
0.7727	Intermediate Similarity	NPC477308
0.7727	Intermediate Similarity	NPC477316
0.7727	Intermediate Similarity	NPC477313
0.7727	Intermediate Similarity	NPC477304
0.7727	Intermediate Similarity	NPC477309
0.7727	Intermediate Similarity	NPC477305
0.7727	Intermediate Similarity	NPC477315
0.7727	Intermediate Similarity	NPC477312
0.7727	Intermediate Similarity	NPC10721
0.7723	Intermediate Similarity	NPC72647
0.7723	Intermediate Similarity	NPC107806
0.7719	Intermediate Similarity	NPC473919
0.7719	Intermediate Similarity	NPC473709
0.7717	Intermediate Similarity	NPC474894
0.7714	Intermediate Similarity	NPC122816
0.7714	Intermediate Similarity	NPC187435
0.7714	Intermediate Similarity	NPC67321
0.7708	Intermediate Similarity	NPC470260
0.7708	Intermediate Similarity	NPC75443
0.7706	Intermediate Similarity	NPC216665
0.7706	Intermediate Similarity	NPC472400
0.77	Intermediate Similarity	NPC221801
0.77	Intermediate Similarity	NPC471765
0.77	Intermediate Similarity	NPC279621
0.77	Intermediate Similarity	NPC476315
0.77	Intermediate Similarity	NPC284194
0.77	Intermediate Similarity	NPC129569
0.77	Intermediate Similarity	NPC211810
0.7699	Intermediate Similarity	NPC162009
0.7699	Intermediate Similarity	NPC257017
0.7692	Intermediate Similarity	NPC194941
0.7685	Intermediate Similarity	NPC317687
0.7684	Intermediate Similarity	NPC311163
0.7679	Intermediate Similarity	NPC157252
0.7679	Intermediate Similarity	NPC471126
0.7679	Intermediate Similarity	NPC145182
0.7679	Intermediate Similarity	NPC475885
0.7679	Intermediate Similarity	NPC471128
0.7677	Intermediate Similarity	NPC256368
0.7677	Intermediate Similarity	NPC105490
0.7677	Intermediate Similarity	NPC140277
0.7677	Intermediate Similarity	NPC159698
0.7677	Intermediate Similarity	NPC161998
0.767	Intermediate Similarity	NPC474709
0.766	Intermediate Similarity	NPC186155
0.766	Intermediate Similarity	NPC78673
0.766	Intermediate Similarity	NPC160517
0.7653	Intermediate Similarity	NPC41838
0.7652	Intermediate Similarity	NPC471939
0.7647	Intermediate Similarity	NPC469551
0.7647	Intermediate Similarity	NPC47024
0.7647	Intermediate Similarity	NPC16601
0.7642	Intermediate Similarity	NPC50124
0.7642	Intermediate Similarity	NPC94377
0.7642	Intermediate Similarity	NPC38948
0.7636	Intermediate Similarity	NPC471816
0.7636	Intermediate Similarity	NPC470075
0.7629	Intermediate Similarity	NPC291875
0.7624	Intermediate Similarity	NPC100912
0.7624	Intermediate Similarity	NPC474395
0.7624	Intermediate Similarity	NPC120446
0.7619	Intermediate Similarity	NPC111952
0.7619	Intermediate Similarity	NPC471206
0.7615	Intermediate Similarity	NPC472757
0.7614	Intermediate Similarity	NPC477303
0.7614	Intermediate Similarity	NPC477311
0.7611	Intermediate Similarity	NPC52839
0.7604	Intermediate Similarity	NPC44538
0.76	Intermediate Similarity	NPC14961
0.76	Intermediate Similarity	NPC270013
0.76	Intermediate Similarity	NPC36954
0.76	Intermediate Similarity	NPC476720
0.7596	Intermediate Similarity	NPC471938
0.7596	Intermediate Similarity	NPC281378
0.7596	Intermediate Similarity	NPC474124
0.7593	Intermediate Similarity	NPC469656
0.7593	Intermediate Similarity	NPC474846
0.7593	Intermediate Similarity	NPC317107
0.7593	Intermediate Similarity	NPC469655
0.7589	Intermediate Similarity	NPC236918
0.7589	Intermediate Similarity	NPC156745
0.7586	Intermediate Similarity	NPC471940
0.7579	Intermediate Similarity	NPC471494
0.7579	Intermediate Similarity	NPC298595
0.7576	Intermediate Similarity	NPC212486
0.7576	Intermediate Similarity	NPC110022
0.7576	Intermediate Similarity	NPC7349
0.7576	Intermediate Similarity	NPC476300
0.7573	Intermediate Similarity	NPC475617
0.757	Intermediate Similarity	NPC206618
0.757	Intermediate Similarity	NPC299590
0.7568	Intermediate Similarity	NPC296822
0.7549	Intermediate Similarity	NPC474213
0.7549	Intermediate Similarity	NPC222303
0.7549	Intermediate Similarity	NPC475068
0.7547	Intermediate Similarity	NPC266514
0.7547	Intermediate Similarity	NPC143609
0.7545	Intermediate Similarity	NPC73314
0.7545	Intermediate Similarity	NPC43213
0.7526	Intermediate Similarity	NPC92370
0.7525	Intermediate Similarity	NPC194132
0.7525	Intermediate Similarity	NPC57664
0.7524	Intermediate Similarity	NPC473577
0.7524	Intermediate Similarity	NPC283850
0.7524	Intermediate Similarity	NPC475585
0.7524	Intermediate Similarity	NPC471937
0.7524	Intermediate Similarity	NPC473543
0.7524	Intermediate Similarity	NPC477127
0.7524	Intermediate Similarity	NPC474550
0.7523	Intermediate Similarity	NPC321272
0.7523	Intermediate Similarity	NPC470025
0.7523	Intermediate Similarity	NPC473877
0.7523	Intermediate Similarity	NPC328074
0.7523	Intermediate Similarity	NPC317460
0.7522	Intermediate Similarity	NPC472759
0.7522	Intermediate Similarity	NPC143755
0.7522	Intermediate Similarity	NPC329080
0.75	Intermediate Similarity	NPC283343
0.75	Intermediate Similarity	NPC316708
0.75	Intermediate Similarity	NPC476081
0.75	Intermediate Similarity	NPC471914
0.75	Intermediate Similarity	NPC472360
0.75	Intermediate Similarity	NPC81386
0.75	Intermediate Similarity	NPC105375
0.75	Intermediate Similarity	NPC476471
0.75	Intermediate Similarity	NPC474247
0.75	Intermediate Similarity	NPC472758
0.75	Intermediate Similarity	NPC200672
0.75	Intermediate Similarity	NPC472214
0.75	Intermediate Similarity	NPC165578
0.75	Intermediate Similarity	NPC61527
0.75	Intermediate Similarity	NPC182826
0.75	Intermediate Similarity	NPC475684
0.75	Intermediate Similarity	NPC273668
0.75	Intermediate Similarity	NPC474035

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 NPC469583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	2049
0.2-0.3	3725
0.3-0.4	2119
0.4-0.5	778
0.5-0.6	237
0.6-0.7	38
0.7-0.8	4
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8854	High Similarity	NPD5344	Discontinued
0.8367	Intermediate Similarity	NPD6648	Approved
0.8298	Intermediate Similarity	NPD7838	Discovery
0.8105	Intermediate Similarity	NPD46	Approved
0.8105	Intermediate Similarity	NPD6698	Approved
0.757	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7516	Approved
0.7212	Intermediate Similarity	NPD4225	Approved
0.7212	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7327	Approved
0.7193	Intermediate Similarity	NPD7328	Approved
0.7064	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7640	Approved
0.6981	Remote Similarity	NPD7639	Approved
0.6957	Remote Similarity	NPD7115	Discovery
0.6909	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6371	Approved
0.6864	Remote Similarity	NPD8380	Approved
0.6864	Remote Similarity	NPD8378	Approved
0.6864	Remote Similarity	NPD8033	Approved
0.6864	Remote Similarity	NPD8379	Approved
0.6864	Remote Similarity	NPD8296	Approved
0.6864	Remote Similarity	NPD8335	Approved
0.6863	Remote Similarity	NPD3168	Discontinued
0.6813	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7983	Approved
0.678	Remote Similarity	NPD8294	Approved
0.678	Remote Similarity	NPD8377	Approved
0.6723	Remote Similarity	NPD7503	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6613	Remote Similarity	NPD7319	Approved
0.6545	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8515	Approved
0.6446	Remote Similarity	NPD6921	Approved
0.6446	Remote Similarity	NPD8516	Approved
0.6446	Remote Similarity	NPD8517	Approved
0.6446	Remote Similarity	NPD8513	Phase 3
0.6444	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8133	Approved
0.6408	Remote Similarity	NPD7524	Approved
0.6396	Remote Similarity	NPD7632	Discontinued
0.6372	Remote Similarity	NPD5357	Phase 1
0.6364	Remote Similarity	NPD6319	Approved
0.6325	Remote Similarity	NPD8297	Approved
0.6325	Remote Similarity	NPD6053	Discontinued
0.6286	Remote Similarity	NPD1695	Approved
0.6271	Remote Similarity	NPD4632	Approved
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD5779	Approved
0.621	Remote Similarity	NPD7829	Approved
0.621	Remote Similarity	NPD7642	Approved
0.621	Remote Similarity	NPD7830	Approved
0.6207	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8074	Phase 3
0.6168	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD371	Approved
0.6121	Remote Similarity	NPD6881	Approved
0.6121	Remote Similarity	NPD6899	Approved
0.6117	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8273	Phase 1
0.6102	Remote Similarity	NPD6649	Approved
0.6102	Remote Similarity	NPD6650	Approved
0.6095	Remote Similarity	NPD4250	Approved
0.6095	Remote Similarity	NPD4251	Approved
0.6087	Remote Similarity	NPD7128	Approved
0.6087	Remote Similarity	NPD6008	Approved
0.6087	Remote Similarity	NPD6402	Approved
0.6087	Remote Similarity	NPD5739	Approved
0.6087	Remote Similarity	NPD6675	Approved
0.608	Remote Similarity	NPD8328	Phase 3
0.608	Remote Similarity	NPD7604	Phase 2
0.6068	Remote Similarity	NPD6372	Approved
0.6068	Remote Similarity	NPD6373	Approved
0.6058	Remote Similarity	NPD1694	Approved
0.6058	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7748	Approved
0.605	Remote Similarity	NPD6882	Approved
0.604	Remote Similarity	NPD4819	Approved
0.604	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4822	Approved
0.604	Remote Similarity	NPD4821	Approved
0.604	Remote Similarity	NPD4820	Approved
0.6036	Remote Similarity	NPD7902	Approved
0.6034	Remote Similarity	NPD6412	Phase 2
0.6034	Remote Similarity	NPD5697	Approved
0.6032	Remote Similarity	NPD7492	Approved
0.6019	Remote Similarity	NPD6695	Phase 3
0.6019	Remote Similarity	NPD7154	Phase 3
0.6019	Remote Similarity	NPD6110	Phase 1
0.6019	Remote Similarity	NPD7515	Phase 2
0.6018	Remote Similarity	NPD4159	Approved
0.6017	Remote Similarity	NPD7102	Approved
0.6017	Remote Similarity	NPD7290	Approved
0.6017	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6616	Approved
0.5984	Remote Similarity	NPD6009	Approved
0.5983	Remote Similarity	NPD7320	Approved
0.5968	Remote Similarity	NPD6054	Approved
0.5966	Remote Similarity	NPD6617	Approved
0.5966	Remote Similarity	NPD6869	Approved
0.5966	Remote Similarity	NPD6847	Approved
0.5966	Remote Similarity	NPD8130	Phase 1
0.5946	Remote Similarity	NPD7839	Suspended
0.5938	Remote Similarity	NPD7078	Approved
0.5932	Remote Similarity	NPD6013	Approved
0.5932	Remote Similarity	NPD6014	Approved
0.5932	Remote Similarity	NPD6012	Approved
0.5926	Remote Similarity	NPD5785	Approved
0.5922	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.592	Remote Similarity	NPD5983	Phase 2
0.5897	Remote Similarity	NPD5701	Approved
0.5891	Remote Similarity	NPD7736	Approved
0.5873	Remote Similarity	NPD6370	Approved
0.5859	Remote Similarity	NPD6336	Discontinued
0.5854	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7505	Discontinued
0.5847	Remote Similarity	NPD6011	Approved
0.5842	Remote Similarity	NPD4271	Approved
0.5842	Remote Similarity	NPD4268	Approved
0.584	Remote Similarity	NPD6059	Approved
0.5833	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6101	Approved
0.5818	Remote Similarity	NPD6399	Phase 3
0.5816	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8293	Discontinued
0.5806	Remote Similarity	NPD7641	Discontinued
0.5804	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7750	Discontinued
0.5794	Remote Similarity	NPD6015	Approved
0.5794	Remote Similarity	NPD6016	Approved
0.5778	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5282	Discontinued
0.5766	Remote Similarity	NPD7900	Approved
0.5758	Remote Similarity	NPD7260	Phase 2
0.5755	Remote Similarity	NPD5363	Approved
0.5752	Remote Similarity	NPD6084	Phase 2
0.5752	Remote Similarity	NPD6083	Phase 2
0.575	Remote Similarity	NPD6421	Discontinued
0.575	Remote Similarity	NPD4634	Approved
0.5748	Remote Similarity	NPD5988	Approved
0.5736	Remote Similarity	NPD8451	Approved
0.5728	Remote Similarity	NPD6931	Approved
0.5728	Remote Similarity	NPD6930	Phase 2
0.5728	Remote Similarity	NPD7525	Registered
0.5727	Remote Similarity	NPD6411	Approved
0.5727	Remote Similarity	NPD8035	Phase 2
0.5727	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD5362	Discontinued
0.5704	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD8448	Approved
0.569	Remote Similarity	NPD5211	Phase 2
0.5688	Remote Similarity	NPD6051	Approved
0.5669	Remote Similarity	NPD8444	Approved
0.5652	Remote Similarity	NPD5286	Approved
0.5652	Remote Similarity	NPD4696	Approved
0.5652	Remote Similarity	NPD5285	Approved
0.5645	Remote Similarity	NPD6274	Approved
0.5635	Remote Similarity	NPD7100	Approved
0.5635	Remote Similarity	NPD7101	Approved
0.5634	Remote Similarity	NPD7625	Phase 1
0.5631	Remote Similarity	NPD7645	Phase 2
0.5631	Remote Similarity	NPD6929	Approved
0.563	Remote Similarity	NPD8415	Approved
0.5619	Remote Similarity	NPD6435	Approved
0.5619	Remote Similarity	NPD5209	Approved
0.5614	Remote Similarity	NPD4755	Approved
0.5607	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD1700	Approved
0.56	Remote Similarity	NPD7500	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