NPASS Compound

Structure

CID245004 OpenBabel06191716042D 26 27 0 0 1 0 0 0 0 0999 V2000 -0.8764 -4.6566 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0896 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0579 -1.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0896 -4.3978 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3143 -3.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 1.7321 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3484 -3.4319 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6175 -3.1730 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 1 8 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 6 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 26 1 1 0 0 0 21 25 1 0 0 0 0 22 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.26
Volume:	399.207
LogP:	3.71
LogD:	3.034
LogS:	-4.298
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	4.835
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.629
MDCK Permeability:	1.9807848730124533e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.746
Plasma Protein Binding (PPB):	86.99883270263672%
Volume Distribution (VD):	1.458
Pgp-substrate:	15.205925941467285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.283
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.231
CYP2D6-inhibitor:	0.125
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	3.39
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.28
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.181
Skin Sensitization:	0.145
Carcinogencity:	0.187
Eye Corrosion:	0.024
Eye Irritation:	0.119
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC245004

Natural Product ID:	NPC245004
*Common Name:**	Vitetrifolin F
IUPAC Name:	[(1S,2R,3S,4R)-1-hydroxy-4-(3-hydroxy-3-methylpent-4-enyl)-3,4,8,8-tetramethyl-1,2,3,5,6,7-hexahydronaphthalen-2-yl] acetate
Synonyms:
Standard InCHIKey:	XKQBKQUOQCQQBX-RRLXMNTOSA-N
Standard InCHI:	InChI=1S/C22H36O4/c1-8-21(6,25)12-13-22(7)14(2)19(26-15(3)23)18(24)17-16(22)10-9-11-20(17,4)5/h8,14,18-19,24-25H,1,9-13H2,2-7H3/t14-,18+,19-,21?,22-/m1/s1
SMILES:	C=CC(C)(CC[C@]1(C)[C@H](C)[C@H]([C@H](C2=C1CCCC2(C)C)O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436602
PubChem CID:	11222285
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21373	Vitex trifolia	Species	Lamiaceae	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[488779]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[488779]

☑ 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 NPC245004 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	183
0.1-0.2	1204
0.2-0.3	4709
0.3-0.4	13844
0.4-0.5	10603
0.5-0.6	7522
0.6-0.7	4181
0.7-0.8	431
0.8-0.85	15
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC20946
0.9518	High Similarity	NPC131329
0.8916	High Similarity	NPC471408
0.8824	High Similarity	NPC35933
0.8636	High Similarity	NPC246028
0.8588	High Similarity	NPC49208
0.8588	High Similarity	NPC23748
0.8556	High Similarity	NPC27918
0.8537	High Similarity	NPC40049
0.8506	High Similarity	NPC175145
0.8506	High Similarity	NPC475069
0.8495	Intermediate Similarity	NPC247233
0.8478	Intermediate Similarity	NPC57664
0.8471	Intermediate Similarity	NPC256112
0.8444	Intermediate Similarity	NPC477574
0.8427	Intermediate Similarity	NPC16265
0.8372	Intermediate Similarity	NPC476927
0.8353	Intermediate Similarity	NPC25554
0.8353	Intermediate Similarity	NPC142163
0.8352	Intermediate Similarity	NPC53555
0.8313	Intermediate Similarity	NPC283619
0.8261	Intermediate Similarity	NPC474922
0.8261	Intermediate Similarity	NPC472360
0.8261	Intermediate Similarity	NPC472416
0.8256	Intermediate Similarity	NPC2524
0.8222	Intermediate Similarity	NPC115607
0.8222	Intermediate Similarity	NPC82876
0.8211	Intermediate Similarity	NPC38855
0.8211	Intermediate Similarity	NPC473510
0.8202	Intermediate Similarity	NPC166857
0.8193	Intermediate Similarity	NPC265588
0.8191	Intermediate Similarity	NPC473244
0.8191	Intermediate Similarity	NPC210337
0.8182	Intermediate Similarity	NPC109528
0.8172	Intermediate Similarity	NPC53565
0.8161	Intermediate Similarity	NPC474789
0.8161	Intermediate Similarity	NPC52108
0.814	Intermediate Similarity	NPC159148
0.814	Intermediate Similarity	NPC170303
0.8132	Intermediate Similarity	NPC78973
0.8132	Intermediate Similarity	NPC473269
0.8118	Intermediate Similarity	NPC242767
0.8118	Intermediate Similarity	NPC100906
0.809	Intermediate Similarity	NPC474970
0.809	Intermediate Similarity	NPC473226
0.8085	Intermediate Similarity	NPC471765
0.8085	Intermediate Similarity	NPC88009
0.8085	Intermediate Similarity	NPC221801
0.8085	Intermediate Similarity	NPC129569
0.8085	Intermediate Similarity	NPC211810
0.8085	Intermediate Similarity	NPC284194
0.8068	Intermediate Similarity	NPC302360
0.8068	Intermediate Similarity	NPC102048
0.8068	Intermediate Similarity	NPC306951
0.8065	Intermediate Similarity	NPC215700
0.8043	Intermediate Similarity	NPC177641
0.8041	Intermediate Similarity	NPC470571
0.8041	Intermediate Similarity	NPC11956
0.8023	Intermediate Similarity	NPC281880
0.8023	Intermediate Similarity	NPC233332
0.8022	Intermediate Similarity	NPC97103
0.8022	Intermediate Similarity	NPC314727
0.8021	Intermediate Similarity	NPC230546
0.8	Intermediate Similarity	NPC83351
0.8	Intermediate Similarity	NPC167891
0.8	Intermediate Similarity	NPC141401
0.798	Intermediate Similarity	NPC470763
0.798	Intermediate Similarity	NPC470767
0.7979	Intermediate Similarity	NPC134067
0.7978	Intermediate Similarity	NPC164424
0.7959	Intermediate Similarity	NPC23584
0.7955	Intermediate Similarity	NPC79945
0.7955	Intermediate Similarity	NPC57370
0.7952	Intermediate Similarity	NPC104644
0.7938	Intermediate Similarity	NPC96784
0.7938	Intermediate Similarity	NPC475617
0.7938	Intermediate Similarity	NPC472554
0.7938	Intermediate Similarity	NPC235920
0.7935	Intermediate Similarity	NPC220216
0.7935	Intermediate Similarity	NPC48732
0.7917	Intermediate Similarity	NPC478056
0.7912	Intermediate Similarity	NPC229612
0.7912	Intermediate Similarity	NPC7280
0.7907	Intermediate Similarity	NPC233295
0.79	Intermediate Similarity	NPC301666
0.7895	Intermediate Similarity	NPC276103
0.7895	Intermediate Similarity	NPC54248
0.7895	Intermediate Similarity	NPC473153
0.7889	Intermediate Similarity	NPC73038
0.7889	Intermediate Similarity	NPC82979
0.7889	Intermediate Similarity	NPC281316
0.7882	Intermediate Similarity	NPC91594
0.7879	Intermediate Similarity	NPC473543
0.7879	Intermediate Similarity	NPC470768
0.7872	Intermediate Similarity	NPC119562
0.7872	Intermediate Similarity	NPC469491
0.7872	Intermediate Similarity	NPC470958
0.7872	Intermediate Similarity	NPC470957
0.7872	Intermediate Similarity	NPC105375
0.7872	Intermediate Similarity	NPC279410
0.7872	Intermediate Similarity	NPC182826
0.7857	Intermediate Similarity	NPC472552
0.7849	Intermediate Similarity	NPC124374
0.7849	Intermediate Similarity	NPC41239
0.7841	Intermediate Similarity	NPC73882
0.7841	Intermediate Similarity	NPC87489
0.7841	Intermediate Similarity	NPC474979
0.7835	Intermediate Similarity	NPC188968
0.7835	Intermediate Similarity	NPC79303
0.7835	Intermediate Similarity	NPC474190
0.7831	Intermediate Similarity	NPC130665
0.7826	Intermediate Similarity	NPC49783
0.7826	Intermediate Similarity	NPC261320
0.7826	Intermediate Similarity	NPC477917
0.7822	Intermediate Similarity	NPC472218
0.7822	Intermediate Similarity	NPC472217
0.7822	Intermediate Similarity	NPC472219
0.7816	Intermediate Similarity	NPC474592
0.7816	Intermediate Similarity	NPC269791
0.7812	Intermediate Similarity	NPC475033
0.7812	Intermediate Similarity	NPC254496
0.7812	Intermediate Similarity	NPC261807
0.7812	Intermediate Similarity	NPC475032
0.7812	Intermediate Similarity	NPC99726
0.7812	Intermediate Similarity	NPC205143
0.7802	Intermediate Similarity	NPC476948
0.7802	Intermediate Similarity	NPC473097
0.7802	Intermediate Similarity	NPC471779
0.7789	Intermediate Similarity	NPC276110
0.7789	Intermediate Similarity	NPC292178
0.7789	Intermediate Similarity	NPC86893
0.7778	Intermediate Similarity	NPC474124
0.7778	Intermediate Similarity	NPC476602
0.7778	Intermediate Similarity	NPC290731
0.7778	Intermediate Similarity	NPC191965
0.7778	Intermediate Similarity	NPC473523
0.7766	Intermediate Similarity	NPC133579
0.7766	Intermediate Similarity	NPC214697
0.7766	Intermediate Similarity	NPC99653
0.7766	Intermediate Similarity	NPC38232
0.7766	Intermediate Similarity	NPC474806
0.7755	Intermediate Similarity	NPC233012
0.7755	Intermediate Similarity	NPC280991
0.7755	Intermediate Similarity	NPC54909
0.7755	Intermediate Similarity	NPC115862
0.7755	Intermediate Similarity	NPC97435
0.7755	Intermediate Similarity	NPC303559
0.7753	Intermediate Similarity	NPC474634
0.7753	Intermediate Similarity	NPC474809
0.7745	Intermediate Similarity	NPC5475
0.7745	Intermediate Similarity	NPC472216
0.7745	Intermediate Similarity	NPC284828
0.7745	Intermediate Similarity	NPC173905
0.7742	Intermediate Similarity	NPC469400
0.7742	Intermediate Similarity	NPC214844
0.7742	Intermediate Similarity	NPC472307
0.7738	Intermediate Similarity	NPC201048
0.7738	Intermediate Similarity	NPC71152
0.7738	Intermediate Similarity	NPC476366
0.7732	Intermediate Similarity	NPC477876
0.7732	Intermediate Similarity	NPC470068
0.7732	Intermediate Similarity	NPC470066
0.7732	Intermediate Similarity	NPC124512
0.7732	Intermediate Similarity	NPC159763
0.7732	Intermediate Similarity	NPC278386
0.7732	Intermediate Similarity	NPC477875
0.7732	Intermediate Similarity	NPC470067
0.7727	Intermediate Similarity	NPC473420
0.7727	Intermediate Similarity	NPC476646
0.7723	Intermediate Similarity	NPC475176
0.7723	Intermediate Similarity	NPC473284
0.7723	Intermediate Similarity	NPC67321
0.7723	Intermediate Similarity	NPC187435
0.7717	Intermediate Similarity	NPC280556
0.7711	Intermediate Similarity	NPC110799
0.7708	Intermediate Similarity	NPC288970
0.7708	Intermediate Similarity	NPC471903
0.7708	Intermediate Similarity	NPC230151
0.7708	Intermediate Similarity	NPC190713
0.7701	Intermediate Similarity	NPC476367
0.7701	Intermediate Similarity	NPC72755
0.77	Intermediate Similarity	NPC152966
0.7692	Intermediate Similarity	NPC329692
0.7692	Intermediate Similarity	NPC137306
0.7692	Intermediate Similarity	NPC84121
0.7692	Intermediate Similarity	NPC261266
0.7692	Intermediate Similarity	NPC131813
0.7692	Intermediate Similarity	NPC322159
0.7692	Intermediate Similarity	NPC325594
0.7692	Intermediate Similarity	NPC255143
0.7692	Intermediate Similarity	NPC476217
0.7684	Intermediate Similarity	NPC178949
0.7684	Intermediate Similarity	NPC96736
0.7684	Intermediate Similarity	NPC87095
0.7684	Intermediate Similarity	NPC469406
0.7684	Intermediate Similarity	NPC105490
0.7684	Intermediate Similarity	NPC211238
0.7683	Intermediate Similarity	NPC471560
0.7683	Intermediate Similarity	NPC473893
0.7677	Intermediate Similarity	NPC472815

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 NPC245004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1712
0.2-0.3	3748
0.3-0.4	2398
0.4-0.5	734
0.5-0.6	322
0.6-0.7	74
0.7-0.8	8
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
0.7732	Intermediate Similarity	NPD4225	Approved
0.7647	Intermediate Similarity	NPD8264	Approved
0.7407	Intermediate Similarity	NPD7115	Discovery
0.74	Intermediate Similarity	NPD5344	Discontinued
0.7396	Intermediate Similarity	NPD5778	Approved
0.7396	Intermediate Similarity	NPD5779	Approved
0.73	Intermediate Similarity	NPD7640	Approved
0.73	Intermediate Similarity	NPD7639	Approved
0.7292	Intermediate Similarity	NPD6411	Approved
0.72	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7113	Intermediate Similarity	NPD7515	Phase 2
0.7111	Intermediate Similarity	NPD7645	Phase 2
0.7083	Intermediate Similarity	NPD6101	Approved
0.7083	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7524	Approved
0.7041	Intermediate Similarity	NPD6399	Phase 3
0.7033	Intermediate Similarity	NPD7525	Registered
0.6961	Remote Similarity	NPD6648	Approved
0.6939	Remote Similarity	NPD7637	Suspended
0.6931	Remote Similarity	NPD7902	Approved
0.6916	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6051	Approved
0.6881	Remote Similarity	NPD8297	Approved
0.6854	Remote Similarity	NPD7339	Approved
0.6854	Remote Similarity	NPD6942	Approved
0.6827	Remote Similarity	NPD7632	Discontinued
0.6822	Remote Similarity	NPD6899	Approved
0.6822	Remote Similarity	NPD6881	Approved
0.6809	Remote Similarity	NPD6695	Phase 3
0.6792	Remote Similarity	NPD7128	Approved
0.6792	Remote Similarity	NPD6402	Approved
0.6792	Remote Similarity	NPD5739	Approved
0.6792	Remote Similarity	NPD6675	Approved
0.6778	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6933	Approved
0.6759	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4786	Approved
0.6737	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5697	Approved
0.6726	Remote Similarity	NPD7328	Approved
0.6726	Remote Similarity	NPD7327	Approved
0.6702	Remote Similarity	NPD3667	Approved
0.6701	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6883	Approved
0.6697	Remote Similarity	NPD7290	Approved
0.6697	Remote Similarity	NPD7102	Approved
0.6696	Remote Similarity	NPD7503	Approved
0.6696	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4748	Discontinued
0.6636	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD8130	Phase 1
0.6636	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD6869	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6847	Approved
0.6634	Remote Similarity	NPD7900	Approved
0.6634	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5362	Discontinued
0.6632	Remote Similarity	NPD7154	Phase 3
0.663	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD368	Approved
0.6609	Remote Similarity	NPD8377	Approved
0.6609	Remote Similarity	NPD8294	Approved
0.6606	Remote Similarity	NPD6373	Approved
0.6606	Remote Similarity	NPD6372	Approved
0.6606	Remote Similarity	NPD6012	Approved
0.6606	Remote Similarity	NPD6014	Approved
0.6606	Remote Similarity	NPD6013	Approved
0.6602	Remote Similarity	NPD6083	Phase 2
0.6602	Remote Similarity	NPD6084	Phase 2
0.66	Remote Similarity	NPD6079	Approved
0.66	Remote Similarity	NPD7983	Approved
0.6598	Remote Similarity	NPD3618	Phase 1
0.6577	Remote Similarity	NPD6882	Approved
0.6574	Remote Similarity	NPD5701	Approved
0.6571	Remote Similarity	NPD4159	Approved
0.6569	Remote Similarity	NPD5695	Phase 3
0.6566	Remote Similarity	NPD5328	Approved
0.6556	Remote Similarity	NPD6926	Approved
0.6556	Remote Similarity	NPD6924	Approved
0.6552	Remote Similarity	NPD8335	Approved
0.6552	Remote Similarity	NPD8380	Approved
0.6552	Remote Similarity	NPD8379	Approved
0.6552	Remote Similarity	NPD8378	Approved
0.6552	Remote Similarity	NPD8296	Approved
0.6545	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3573	Approved
0.6531	Remote Similarity	NPD7750	Discontinued
0.6514	Remote Similarity	NPD6686	Approved
0.6509	Remote Similarity	NPD5211	Phase 2
0.6505	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6698	Approved
0.65	Remote Similarity	NPD46	Approved
0.6495	Remote Similarity	NPD1696	Phase 3
0.6495	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6931	Approved
0.6489	Remote Similarity	NPD6930	Phase 2
0.6489	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7332	Phase 2
0.6489	Remote Similarity	NPD7514	Phase 3
0.6486	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6319	Approved
0.6458	Remote Similarity	NPD5332	Approved
0.6458	Remote Similarity	NPD5331	Approved
0.6452	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD4271	Approved
0.6436	Remote Similarity	NPD8034	Phase 2
0.6436	Remote Similarity	NPD8035	Phase 2
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6421	Remote Similarity	NPD4790	Discontinued
0.641	Remote Similarity	NPD8513	Phase 3
0.641	Remote Similarity	NPD8516	Approved
0.641	Remote Similarity	NPD8515	Approved
0.641	Remote Similarity	NPD8517	Approved
0.64	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5141	Approved
0.6383	Remote Similarity	NPD6929	Approved
0.6374	Remote Similarity	NPD4784	Approved
0.6374	Remote Similarity	NPD4785	Approved
0.6373	Remote Similarity	NPD4202	Approved
0.6354	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4270	Approved
0.6354	Remote Similarity	NPD4269	Approved
0.6348	Remote Similarity	NPD6009	Approved
0.6348	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5222	Approved
0.6346	Remote Similarity	NPD5221	Approved
0.6337	Remote Similarity	NPD5785	Approved
0.6333	Remote Similarity	NPD7151	Approved
0.6333	Remote Similarity	NPD7150	Approved
0.6333	Remote Similarity	NPD7152	Approved
0.6333	Remote Similarity	NPD7507	Approved
0.6321	Remote Similarity	NPD5286	Approved
0.6321	Remote Similarity	NPD4696	Approved
0.6321	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD7509	Discontinued
0.6304	Remote Similarity	NPD8039	Approved
0.6303	Remote Similarity	NPD7604	Phase 2
0.63	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6903	Approved
0.63	Remote Similarity	NPD5737	Approved
0.63	Remote Similarity	NPD6672	Approved
0.6293	Remote Similarity	NPD6335	Approved
0.6286	Remote Similarity	NPD4755	Approved
0.6286	Remote Similarity	NPD5173	Approved
0.6279	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7145	Approved
0.6275	Remote Similarity	NPD5281	Approved
0.6275	Remote Similarity	NPD7087	Discontinued
0.6275	Remote Similarity	NPD5284	Approved
0.6273	Remote Similarity	NPD6412	Phase 2
0.6273	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5983	Phase 2
0.6263	Remote Similarity	NPD4623	Approved
0.6263	Remote Similarity	NPD5786	Approved
0.6263	Remote Similarity	NPD4519	Discontinued
0.6262	Remote Similarity	NPD5223	Approved
0.6261	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7492	Approved
0.6239	Remote Similarity	NPD7100	Approved
0.6239	Remote Similarity	NPD7101	Approved
0.6226	Remote Similarity	NPD5696	Approved
0.6224	Remote Similarity	NPD3666	Approved
0.6224	Remote Similarity	NPD3665	Phase 1
0.6224	Remote Similarity	NPD3133	Approved
0.6224	Remote Similarity	NPD3668	Phase 3
0.6222	Remote Similarity	NPD7143	Approved
0.6222	Remote Similarity	NPD7144	Approved
0.6211	Remote Similarity	NPD4195	Approved
0.6207	Remote Similarity	NPD6317	Approved
0.6204	Remote Similarity	NPD5226	Approved
0.6204	Remote Similarity	NPD4633	Approved
0.6204	Remote Similarity	NPD5225	Approved
0.6204	Remote Similarity	NPD5224	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