NPASS Compound

Structure

NPC474532 OpenBabel07101719132D 35 37 0 0 1 0 0 0 0 0999 V2000 -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 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -3.5000 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 -8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -4.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6603 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 15 1 0 0 0 0 3 16 1 0 0 0 0 4 12 1 0 0 0 0 4 21 1 0 0 0 0 5 9 1 0 0 0 0 5 22 2 0 0 0 0 6 10 2 0 0 0 0 6 22 1 0 0 0 0 7 11 1 0 0 0 0 8 13 2 0 0 0 0 8 22 1 0 0 0 0 9 24 2 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 2 0 0 0 0 13 27 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 35 1 0 0 0 0 19 29 1 0 0 0 0 19 31 1 0 0 0 0 20 29 1 0 0 0 0 20 32 1 0 0 0 0 21 1 1 6 0 0 0 21 25 1 0 0 0 0 23 7 1 6 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 28 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	521.393
LogP:	4.106
LogD:	3.146
LogS:	-4.034
# Rotatable Bonds:	12
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	4.515
Fsp3:	0.621
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.782
MDCK Permeability:	1.5785502910148352e-05
Pgp-inhibitor:	0.246
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.389
Plasma Protein Binding (PPB):	95.20258331298828%
Volume Distribution (VD):	0.71
Pgp-substrate:	2.6346328258514404%

ADMET: Metabolism

CYP1A2-inhibitor:	0.291
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.297
CYP2C19-substrate:	0.208
CYP2C9-inhibitor:	0.718
CYP2C9-substrate:	0.302
CYP2D6-inhibitor:	0.474
CYP2D6-substrate:	0.382
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	6.144
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.288
Carcinogencity:	0.724
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC474532

Natural Product ID:	NPC474532
*Common Name:**	Guadichaudol C
IUPAC Name:	[(2S)-2-[2-[(2S,8aR)-5,5-bis(hydroxymethyl)-2,8a-dimethyl-1,2,3,6,7,8-hexahydronaphthalen-1-yl]ethyl]-4-hydroxybutyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	guadichaudol C
Standard InCHIKey:	WKYXCYBYTMQMJO-IUHYZJFXSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-21-4-12-26-28(2,15-3-16-29(26,19-31)20-32)25(21)11-7-23(14-17-30)18-35-27(34)13-8-22-5-9-24(33)10-6-22/h5-6,8-10,12-13,21,23,25,30-33H,3-4,7,11,14-20H2,1-2H3/b13-8+/t21-,23-,25?,28+/m0/s1
SMILES:	CC1CC=C2C(C1CCC(CCO)COC(=O)C=CC3=CC=C(C=C3)O)(CCCC2(CO)CO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471180
PubChem CID:	44575642
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16499330]
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7931367]
NPO258	Baccharis gaudichaudiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO258	Baccharis gaudichaudiana	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
ED50	8

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	19.3	ug ml-1	PMID[449324]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	12.4	ug ml-1	PMID[449324]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[449324]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	13.1	ug ml-1	PMID[449324]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	11.2	ug ml-1	PMID[449324]
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.4	ug ml-1	PMID[449324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	19.0	ug ml-1	PMID[449324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.7	ug ml-1	PMID[449324]

☑ 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 NPC474532 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	218
0.1-0.2	1059
0.2-0.3	2225
0.3-0.4	5288
0.4-0.5	11422
0.5-0.6	8364
0.6-0.7	11763
0.7-0.8	2270
0.8-0.85	77
0.85-0.9	7
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9339	High Similarity	NPC265413
0.9339	High Similarity	NPC10154
0.9106	High Similarity	NPC137416
0.8968	High Similarity	NPC86257
0.8931	High Similarity	NPC139243
0.8931	High Similarity	NPC116742
0.8864	High Similarity	NPC470617
0.8864	High Similarity	NPC470616
0.8855	High Similarity	NPC22676
0.8855	High Similarity	NPC198621
0.8855	High Similarity	NPC475482
0.8855	High Similarity	NPC216940
0.8779	High Similarity	NPC249817
0.8769	High Similarity	NPC11266
0.8722	High Similarity	NPC155192
0.8722	High Similarity	NPC473591
0.8722	High Similarity	NPC271494
0.8702	High Similarity	NPC173569
0.8702	High Similarity	NPC477874
0.8672	High Similarity	NPC288290
0.8667	High Similarity	NPC204644
0.8667	High Similarity	NPC235557
0.8657	High Similarity	NPC472801
0.8647	High Similarity	NPC182249
0.8644	High Similarity	NPC139946
0.8626	High Similarity	NPC194970
0.8603	High Similarity	NPC26045
0.8571	High Similarity	NPC471152
0.856	High Similarity	NPC478058
0.8559	High Similarity	NPC183700
0.8527	High Similarity	NPC30174
0.8525	High Similarity	NPC122117
0.8519	High Similarity	NPC304110
0.8519	High Similarity	NPC27518
0.8478	Intermediate Similarity	NPC320734
0.8467	Intermediate Similarity	NPC25491
0.8409	Intermediate Similarity	NPC475457
0.8409	Intermediate Similarity	NPC475346
0.8409	Intermediate Similarity	NPC475627
0.8409	Intermediate Similarity	NPC18982
0.8403	Intermediate Similarity	NPC63345
0.8394	Intermediate Similarity	NPC310621
0.8382	Intermediate Similarity	NPC172311
0.837	Intermediate Similarity	NPC76032
0.837	Intermediate Similarity	NPC132723
0.837	Intermediate Similarity	NPC248287
0.837	Intermediate Similarity	NPC234548
0.8321	Intermediate Similarity	NPC35212
0.8305	Intermediate Similarity	NPC260952
0.8293	Intermediate Similarity	NPC470820
0.8284	Intermediate Similarity	NPC472804
0.8261	Intermediate Similarity	NPC252133
0.8261	Intermediate Similarity	NPC469447
0.8261	Intermediate Similarity	NPC477873
0.8248	Intermediate Similarity	NPC473612
0.8244	Intermediate Similarity	NPC131684
0.8239	Intermediate Similarity	NPC87630
0.8239	Intermediate Similarity	NPC116292
0.8239	Intermediate Similarity	NPC208785
0.8239	Intermediate Similarity	NPC145527
0.8239	Intermediate Similarity	NPC179128
0.8239	Intermediate Similarity	NPC470618
0.8239	Intermediate Similarity	NPC267469
0.8239	Intermediate Similarity	NPC470619
0.8235	Intermediate Similarity	NPC206341
0.8227	Intermediate Similarity	NPC325032
0.8227	Intermediate Similarity	NPC477483
0.8222	Intermediate Similarity	NPC476699
0.8222	Intermediate Similarity	NPC154485
0.8222	Intermediate Similarity	NPC471872
0.8214	Intermediate Similarity	NPC208293
0.8188	Intermediate Similarity	NPC20631
0.8188	Intermediate Similarity	NPC93640
0.8175	Intermediate Similarity	NPC260832
0.8175	Intermediate Similarity	NPC471875
0.8175	Intermediate Similarity	NPC135467
0.8167	Intermediate Similarity	NPC471954
0.8167	Intermediate Similarity	NPC75272
0.816	Intermediate Similarity	NPC203124
0.8156	Intermediate Similarity	NPC472936
0.8156	Intermediate Similarity	NPC472938
0.8156	Intermediate Similarity	NPC472937
0.8154	Intermediate Similarity	NPC471929
0.8154	Intermediate Similarity	NPC471930
0.8154	Intermediate Similarity	NPC471935
0.8145	Intermediate Similarity	NPC471936
0.8143	Intermediate Similarity	NPC280717
0.8143	Intermediate Similarity	NPC307205
0.8143	Intermediate Similarity	NPC271607
0.8143	Intermediate Similarity	NPC53520
0.8134	Intermediate Similarity	NPC185777
0.813	Intermediate Similarity	NPC41851
0.8125	Intermediate Similarity	NPC327070
0.8125	Intermediate Similarity	NPC325301
0.812	Intermediate Similarity	NPC304638
0.8115	Intermediate Similarity	NPC228425
0.8112	Intermediate Similarity	NPC35160
0.8112	Intermediate Similarity	NPC162569
0.811	Intermediate Similarity	NPC470848
0.811	Intermediate Similarity	NPC470849
0.8106	Intermediate Similarity	NPC117899
0.8095	Intermediate Similarity	NPC42657
0.8095	Intermediate Similarity	NPC263386
0.8095	Intermediate Similarity	NPC141791
0.8088	Intermediate Similarity	NPC120852
0.8083	Intermediate Similarity	NPC470039
0.808	Intermediate Similarity	NPC477136
0.808	Intermediate Similarity	NPC476266
0.8077	Intermediate Similarity	NPC45821
0.8077	Intermediate Similarity	NPC275576
0.8067	Intermediate Similarity	NPC135464
0.8067	Intermediate Similarity	NPC92623
0.8062	Intermediate Similarity	NPC472373
0.8047	Intermediate Similarity	NPC475328
0.8045	Intermediate Similarity	NPC249425
0.8042	Intermediate Similarity	NPC473719
0.803	Intermediate Similarity	NPC469930
0.803	Intermediate Similarity	NPC176590
0.803	Intermediate Similarity	NPC193203
0.8029	Intermediate Similarity	NPC477592
0.8029	Intermediate Similarity	NPC131198
0.8017	Intermediate Similarity	NPC79543
0.8016	Intermediate Similarity	NPC309434
0.8015	Intermediate Similarity	NPC169913
0.8015	Intermediate Similarity	NPC71610
0.8014	Intermediate Similarity	NPC235195
0.8014	Intermediate Similarity	NPC19862
0.8	Intermediate Similarity	NPC308828
0.8	Intermediate Similarity	NPC472591
0.8	Intermediate Similarity	NPC471758
0.8	Intermediate Similarity	NPC475579
0.8	Intermediate Similarity	NPC473773
0.7986	Intermediate Similarity	NPC138149
0.7986	Intermediate Similarity	NPC472939
0.7985	Intermediate Similarity	NPC191395
0.7985	Intermediate Similarity	NPC46137
0.7985	Intermediate Similarity	NPC18798
0.7985	Intermediate Similarity	NPC235294
0.7984	Intermediate Similarity	NPC121168
0.7984	Intermediate Similarity	NPC12016
0.7984	Intermediate Similarity	NPC268160
0.7983	Intermediate Similarity	NPC154899
0.7983	Intermediate Similarity	NPC233396
0.7983	Intermediate Similarity	NPC127676
0.797	Intermediate Similarity	NPC470747
0.7969	Intermediate Similarity	NPC164852
0.7967	Intermediate Similarity	NPC62867
0.7967	Intermediate Similarity	NPC26615
0.7967	Intermediate Similarity	NPC177962
0.7958	Intermediate Similarity	NPC66894
0.7958	Intermediate Similarity	NPC8102
0.7956	Intermediate Similarity	NPC470733
0.7955	Intermediate Similarity	NPC288416
0.7955	Intermediate Similarity	NPC230331
0.7955	Intermediate Similarity	NPC66331
0.7953	Intermediate Similarity	NPC470214
0.7953	Intermediate Similarity	NPC470215
0.7953	Intermediate Similarity	NPC109371
0.7953	Intermediate Similarity	NPC151197
0.7951	Intermediate Similarity	NPC133308
0.7951	Intermediate Similarity	NPC296683
0.7949	Intermediate Similarity	NPC253746
0.7941	Intermediate Similarity	NPC27394
0.7939	Intermediate Similarity	NPC4286
0.7939	Intermediate Similarity	NPC76119
0.7931	Intermediate Similarity	NPC118033
0.7926	Intermediate Similarity	NPC165612
0.7923	Intermediate Similarity	NPC470815
0.792	Intermediate Similarity	NPC147179
0.792	Intermediate Similarity	NPC35797
0.792	Intermediate Similarity	NPC192948
0.792	Intermediate Similarity	NPC474967
0.792	Intermediate Similarity	NPC296526
0.7917	Intermediate Similarity	NPC279442
0.7917	Intermediate Similarity	NPC298647
0.7917	Intermediate Similarity	NPC273358
0.7907	Intermediate Similarity	NPC251259
0.7907	Intermediate Similarity	NPC147654
0.7903	Intermediate Similarity	NPC190212
0.7902	Intermediate Similarity	NPC470330
0.7895	Intermediate Similarity	NPC93632
0.7895	Intermediate Similarity	NPC229894
0.7891	Intermediate Similarity	NPC318581
0.7891	Intermediate Similarity	NPC328485
0.7891	Intermediate Similarity	NPC477037
0.7891	Intermediate Similarity	NPC325544
0.7886	Intermediate Similarity	NPC234376
0.7886	Intermediate Similarity	NPC470770
0.7886	Intermediate Similarity	NPC266937
0.7886	Intermediate Similarity	NPC470355
0.7883	Intermediate Similarity	NPC279463
0.7883	Intermediate Similarity	NPC43353
0.7879	Intermediate Similarity	NPC110211
0.7879	Intermediate Similarity	NPC471157
0.7879	Intermediate Similarity	NPC61181
0.7879	Intermediate Similarity	NPC204579
0.7874	Intermediate Similarity	NPC48342
0.7874	Intermediate Similarity	NPC254233
0.7874	Intermediate Similarity	NPC86198
0.7874	Intermediate Similarity	NPC275519

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 NPC474532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	732
0.2-0.3	1325
0.3-0.4	2397
0.4-0.5	2369
0.5-0.6	1400
0.6-0.7	653
0.7-0.8	71
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
0.8321	Intermediate Similarity	NPD8166	Discontinued
0.8231	Intermediate Similarity	NPD5736	Approved
0.7985	Intermediate Similarity	NPD6663	Approved
0.7926	Intermediate Similarity	NPD4140	Approved
0.7874	Intermediate Similarity	NPD3091	Approved
0.7803	Intermediate Similarity	NPD3094	Phase 2
0.7752	Intermediate Similarity	NPD4626	Approved
0.7752	Intermediate Similarity	NPD2932	Approved
0.7714	Intermediate Similarity	NPD7266	Discontinued
0.7712	Intermediate Similarity	NPD3020	Approved
0.7674	Intermediate Similarity	NPD5691	Approved
0.7664	Intermediate Similarity	NPD4060	Phase 1
0.7634	Intermediate Similarity	NPD3092	Approved
0.7623	Intermediate Similarity	NPD3134	Approved
0.7615	Intermediate Similarity	NPD3095	Discontinued
0.7615	Intermediate Similarity	NPD3019	Approved
0.7552	Intermediate Similarity	NPD7003	Approved
0.7552	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4628	Phase 3
0.7534	Intermediate Similarity	NPD6273	Approved
0.7521	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD4198	Discontinued
0.7458	Intermediate Similarity	NPD2860	Approved
0.7458	Intermediate Similarity	NPD2859	Approved
0.7445	Intermediate Similarity	NPD7095	Approved
0.7424	Intermediate Similarity	NPD3496	Discontinued
0.7419	Intermediate Similarity	NPD1358	Approved
0.7407	Intermediate Similarity	NPD2797	Approved
0.7402	Intermediate Similarity	NPD5535	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD5327	Phase 3
0.7383	Intermediate Similarity	NPD7458	Discontinued
0.7373	Intermediate Similarity	NPD2933	Approved
0.7373	Intermediate Similarity	NPD2934	Approved
0.7357	Intermediate Similarity	NPD5735	Approved
0.7353	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4059	Approved
0.7338	Intermediate Similarity	NPD8032	Phase 2
0.7333	Intermediate Similarity	NPD1283	Approved
0.7329	Intermediate Similarity	NPD7236	Approved
0.7328	Intermediate Similarity	NPD7741	Discontinued
0.7328	Intermediate Similarity	NPD9545	Approved
0.7319	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3021	Approved
0.7302	Intermediate Similarity	NPD3022	Approved
0.7286	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3620	Phase 2
0.7286	Intermediate Similarity	NPD2979	Phase 3
0.7273	Intermediate Similarity	NPD5585	Approved
0.7266	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7635	Approved
0.7266	Intermediate Similarity	NPD3268	Approved
0.7259	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7097	Phase 1
0.7246	Intermediate Similarity	NPD4908	Phase 1
0.7244	Intermediate Similarity	NPD8127	Discontinued
0.7234	Intermediate Similarity	NPD5124	Phase 1
0.7234	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD4624	Approved
0.7222	Intermediate Similarity	NPD5762	Approved
0.7222	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5763	Approved
0.7206	Intermediate Similarity	NPD8651	Approved
0.7203	Intermediate Similarity	NPD2799	Discontinued
0.7192	Intermediate Similarity	NPD3750	Approved
0.7188	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6353	Approved
0.7167	Intermediate Similarity	NPD1809	Phase 2
0.7164	Intermediate Similarity	NPD3847	Discontinued
0.7164	Intermediate Similarity	NPD3026	Approved
0.7164	Intermediate Similarity	NPD3023	Approved
0.7154	Intermediate Similarity	NPD5951	Approved
0.7154	Intermediate Similarity	NPD2629	Approved
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3025	Approved
0.7143	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7132	Intermediate Similarity	NPD7843	Approved
0.7123	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1281	Approved
0.7111	Intermediate Similarity	NPD1610	Phase 2
0.7111	Intermediate Similarity	NPD422	Phase 1
0.7111	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6647	Phase 2
0.7092	Intermediate Similarity	NPD6233	Phase 2
0.7087	Intermediate Similarity	NPD2684	Approved
0.7086	Intermediate Similarity	NPD7239	Suspended
0.7077	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4110	Phase 3
0.7073	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7008	Discontinued
0.7063	Intermediate Similarity	NPD4097	Suspended
0.7063	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.705	Intermediate Similarity	NPD2861	Phase 2
0.7045	Intermediate Similarity	NPD9493	Approved
0.704	Intermediate Similarity	NPD5909	Discontinued
0.7034	Intermediate Similarity	NPD2438	Suspended
0.7034	Intermediate Similarity	NPD5405	Approved
0.7034	Intermediate Similarity	NPD5408	Approved
0.7034	Intermediate Similarity	NPD5404	Approved
0.7034	Intermediate Similarity	NPD5406	Approved
0.7031	Intermediate Similarity	NPD4750	Phase 3
0.7029	Intermediate Similarity	NPD1164	Approved
0.7029	Intermediate Similarity	NPD6362	Approved
0.7021	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6798	Discontinued
0.7007	Intermediate Similarity	NPD4359	Approved
0.7007	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD845	Approved
0.6987	Remote Similarity	NPD7768	Phase 2
0.6986	Remote Similarity	NPD2346	Discontinued
0.6985	Remote Similarity	NPD1611	Approved
0.6985	Remote Similarity	NPD1535	Discovery
0.698	Remote Similarity	NPD6667	Approved
0.698	Remote Similarity	NPD6666	Approved
0.6978	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6671	Approved
0.6968	Remote Similarity	NPD7819	Suspended
0.6967	Remote Similarity	NPD288	Approved
0.6966	Remote Similarity	NPD4308	Phase 3
0.6966	Remote Similarity	NPD7743	Approved
0.6966	Remote Similarity	NPD7742	Approved
0.6963	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5125	Phase 3
0.6963	Remote Similarity	NPD5126	Approved
0.6963	Remote Similarity	NPD1751	Approved
0.6963	Remote Similarity	NPD1778	Approved
0.6963	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3027	Phase 3
0.6947	Remote Similarity	NPD5283	Phase 1
0.6947	Remote Similarity	NPD6010	Discontinued
0.6947	Remote Similarity	NPD2234	Approved
0.6947	Remote Similarity	NPD2229	Approved
0.6947	Remote Similarity	NPD1241	Discontinued
0.6947	Remote Similarity	NPD2228	Approved
0.694	Remote Similarity	NPD1894	Discontinued
0.6934	Remote Similarity	NPD1481	Phase 2
0.6929	Remote Similarity	NPD968	Approved
0.6923	Remote Similarity	NPD6346	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD6099	Approved
0.6918	Remote Similarity	NPD2531	Phase 2
0.6918	Remote Similarity	NPD6100	Approved
0.6913	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3267	Approved
0.6906	Remote Similarity	NPD3266	Approved
0.6903	Remote Similarity	NPD37	Approved
0.6901	Remote Similarity	NPD2313	Discontinued
0.6897	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1651	Approved
0.6889	Remote Similarity	NPD4093	Discontinued
0.6885	Remote Similarity	NPD844	Approved
0.6884	Remote Similarity	NPD4749	Approved
0.6884	Remote Similarity	NPD6582	Phase 2
0.6884	Remote Similarity	NPD6583	Phase 3
0.6883	Remote Similarity	NPD7028	Phase 2
0.688	Remote Similarity	NPD940	Approved
0.688	Remote Similarity	NPD846	Approved
0.6879	Remote Similarity	NPD2614	Approved
0.6879	Remote Similarity	NPD6832	Phase 2
0.6879	Remote Similarity	NPD4966	Approved
0.6879	Remote Similarity	NPD4965	Approved
0.6879	Remote Similarity	NPD4967	Phase 2
0.6875	Remote Similarity	NPD4340	Discontinued
0.6875	Remote Similarity	NPD2342	Discontinued
0.6875	Remote Similarity	NPD230	Phase 1
0.6871	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6005	Phase 3
0.6871	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6002	Phase 3
0.6871	Remote Similarity	NPD6004	Phase 3
0.6871	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6858	Approved
0.687	Remote Similarity	NPD7094	Approved
0.6867	Remote Similarity	NPD7440	Discontinued
0.6857	Remote Similarity	NPD2798	Approved
0.6857	Remote Similarity	NPD6584	Phase 3
0.6849	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7033	Discontinued
0.6849	Remote Similarity	NPD3748	Approved
0.6849	Remote Similarity	NPD4108	Discontinued
0.6846	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2668	Approved
0.6838	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2667	Approved
0.6835	Remote Similarity	NPD6696	Suspended
0.6835	Remote Similarity	NPD1876	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