NPASS Compound

Structure

NPC25554 OpenBabel07101718222D 32 33 0 0 1 0 0 0 0 0999 V2000 0.8660 3.5000 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 -2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 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 1.7321 0.0000 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 -0.8660 1.5000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -1.7321 6.0000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 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 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 30 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 27 2 0 0 0 0 18 30 1 0 0 0 0 19 28 2 0 0 0 0 19 31 1 0 0 0 0 20 29 2 0 0 0 0 20 32 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 25 1 0 0 0 0 24 26 1 6 0 0 0 26 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.28
Volume:	480.698
LogP:	4.837
LogD:	3.83
LogS:	-4.207
# Rotatable Bonds:	10
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.299
Synthetic Accessibility Score:	4.338
Fsp3:	0.731
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:	-4.827
MDCK Permeability:	1.2268187674635556e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.669
30% Bioavailability (F30%):	0.739

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.754
Plasma Protein Binding (PPB):	87.28377532958984%
Volume Distribution (VD):	1.607
Pgp-substrate:	15.225132942199707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.149
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.825
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	3.778
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.786
Drug-inuced Liver Injury (DILI):	0.801
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.598
Carcinogencity:	0.102
Eye Corrosion:	0.219
Eye Irritation:	0.094
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC25554

Natural Product ID:	NPC25554
*Common Name:**	6Beta,7Alpha,15-Triacetoxylabda-8,13E-Diene
IUPAC Name:	[(E)-5-[(3S,4S,4aS,8aS)-3,4-diacetyloxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl] acetate
Synonyms:
Standard InCHIKey:	ZCSONGATRIIYBY-WBAUYTFCSA-N
Standard InCHI:	InChI=1S/C26H40O6/c1-16(12-15-30-18(3)27)10-11-21-17(2)22(31-19(4)28)23(32-20(5)29)24-25(6,7)13-9-14-26(21,24)8/h12,22-24H,9-11,13-15H2,1-8H3/b16-12+/t22-,23+,24-,26+/m0/s1
SMILES:	C/C(=CCOC(=O)C)/CCC1=C(C)[C@@H]([C@H]([C@H]2C(C)(C)CCC[C@]12C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL267935
PubChem CID:	24853963
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO26696	Trimusculus costatus	Species	Trimusculidae	Eukaryota	n.a.	South African	n.a.	PMID[18288809]
NPO26696	Trimusculus costatus	Species	Trimusculidae	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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	84000.0	nM	PMID[490018]

☑ 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 NPC25554 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	192
0.1-0.2	1256
0.2-0.3	4817
0.3-0.4	14716
0.4-0.5	9582
0.5-0.6	7293
0.6-0.7	4210
0.7-0.8	607
0.8-0.85	17
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC35933
0.9114	High Similarity	NPC471218
0.9036	High Similarity	NPC246028
0.8861	High Similarity	NPC233332
0.8795	High Similarity	NPC131329
0.8642	High Similarity	NPC256112
0.8625	High Similarity	NPC469802
0.8588	High Similarity	NPC20946
0.8554	High Similarity	NPC474013
0.8537	High Similarity	NPC49208
0.85	High Similarity	NPC242767
0.8471	Intermediate Similarity	NPC473879
0.8452	Intermediate Similarity	NPC286153
0.8452	Intermediate Similarity	NPC102996
0.8434	Intermediate Similarity	NPC96055
0.8409	Intermediate Similarity	NPC472416
0.8409	Intermediate Similarity	NPC472360
0.8353	Intermediate Similarity	NPC166857
0.8353	Intermediate Similarity	NPC245004
0.8353	Intermediate Similarity	NPC102640
0.8313	Intermediate Similarity	NPC23748
0.8313	Intermediate Similarity	NPC132386
0.8295	Intermediate Similarity	NPC53555
0.8293	Intermediate Similarity	NPC170303
0.8276	Intermediate Similarity	NPC78973
0.8256	Intermediate Similarity	NPC93411
0.8256	Intermediate Similarity	NPC69713
0.8256	Intermediate Similarity	NPC477128
0.8235	Intermediate Similarity	NPC220478
0.8222	Intermediate Similarity	NPC211810
0.8222	Intermediate Similarity	NPC284194
0.8222	Intermediate Similarity	NPC88009
0.8222	Intermediate Similarity	NPC471765
0.8222	Intermediate Similarity	NPC221801
0.8193	Intermediate Similarity	NPC286786
0.8182	Intermediate Similarity	NPC177641
0.8182	Intermediate Similarity	NPC477574
0.8171	Intermediate Similarity	NPC269791
0.8161	Intermediate Similarity	NPC261320
0.8161	Intermediate Similarity	NPC82876
0.8152	Intermediate Similarity	NPC473510
0.814	Intermediate Similarity	NPC476600
0.8132	Intermediate Similarity	NPC473244
0.8132	Intermediate Similarity	NPC210337
0.8111	Intermediate Similarity	NPC471372
0.8111	Intermediate Similarity	NPC472189
0.8111	Intermediate Similarity	NPC471362
0.8095	Intermediate Similarity	NPC476927
0.8095	Intermediate Similarity	NPC474193
0.8095	Intermediate Similarity	NPC12283
0.8072	Intermediate Similarity	NPC108476
0.8072	Intermediate Similarity	NPC142163
0.8072	Intermediate Similarity	NPC195334
0.8072	Intermediate Similarity	NPC290495
0.8068	Intermediate Similarity	NPC220216
0.8065	Intermediate Similarity	NPC472554
0.8065	Intermediate Similarity	NPC475617
0.8049	Intermediate Similarity	NPC44083
0.8049	Intermediate Similarity	NPC153987
0.8046	Intermediate Similarity	NPC106332
0.8025	Intermediate Similarity	NPC283619
0.8023	Intermediate Similarity	NPC474970
0.8023	Intermediate Similarity	NPC131813
0.8022	Intermediate Similarity	NPC171598
0.8022	Intermediate Similarity	NPC94905
0.8022	Intermediate Similarity	NPC8954
0.8	Intermediate Similarity	NPC38830
0.8	Intermediate Similarity	NPC470697
0.8	Intermediate Similarity	NPC306951
0.8	Intermediate Similarity	NPC182826
0.8	Intermediate Similarity	NPC105375
0.7979	Intermediate Similarity	NPC11956
0.7979	Intermediate Similarity	NPC472552
0.7979	Intermediate Similarity	NPC475344
0.7979	Intermediate Similarity	NPC476471
0.7978	Intermediate Similarity	NPC49420
0.7978	Intermediate Similarity	NPC234335
0.7978	Intermediate Similarity	NPC124374
0.7978	Intermediate Similarity	NPC329842
0.7957	Intermediate Similarity	NPC474190
0.7957	Intermediate Similarity	NPC38855
0.7957	Intermediate Similarity	NPC230546
0.7955	Intermediate Similarity	NPC293044
0.7955	Intermediate Similarity	NPC473647
0.7955	Intermediate Similarity	NPC177141
0.7935	Intermediate Similarity	NPC472188
0.7935	Intermediate Similarity	NPC73911
0.7931	Intermediate Similarity	NPC471779
0.7927	Intermediate Similarity	NPC184737
0.7912	Intermediate Similarity	NPC474909
0.7912	Intermediate Similarity	NPC276110
0.7907	Intermediate Similarity	NPC472442
0.7895	Intermediate Similarity	NPC23584
0.7895	Intermediate Similarity	NPC474124
0.7889	Intermediate Similarity	NPC99653
0.7889	Intermediate Similarity	NPC7349
0.7882	Intermediate Similarity	NPC472440
0.7882	Intermediate Similarity	NPC477124
0.7882	Intermediate Similarity	NPC222358
0.7872	Intermediate Similarity	NPC473160
0.7867	Intermediate Similarity	NPC329698
0.7865	Intermediate Similarity	NPC221111
0.7865	Intermediate Similarity	NPC280149
0.7857	Intermediate Similarity	NPC159148
0.7849	Intermediate Similarity	NPC476800
0.7849	Intermediate Similarity	NPC318917
0.7849	Intermediate Similarity	NPC247233
0.7849	Intermediate Similarity	NPC471366
0.7849	Intermediate Similarity	NPC472186
0.7841	Intermediate Similarity	NPC24816
0.7831	Intermediate Similarity	NPC100906
0.7831	Intermediate Similarity	NPC233295
0.7826	Intermediate Similarity	NPC129569
0.7816	Intermediate Similarity	NPC475069
0.7816	Intermediate Similarity	NPC473226
0.7816	Intermediate Similarity	NPC175145
0.7816	Intermediate Similarity	NPC329692
0.7816	Intermediate Similarity	NPC471219
0.7812	Intermediate Similarity	NPC473543
0.7805	Intermediate Similarity	NPC470750
0.7805	Intermediate Similarity	NPC470751
0.7805	Intermediate Similarity	NPC189206
0.7802	Intermediate Similarity	NPC105490
0.7802	Intermediate Similarity	NPC477130
0.7802	Intermediate Similarity	NPC477129
0.7802	Intermediate Similarity	NPC91010
0.7802	Intermediate Similarity	NPC140277
0.7802	Intermediate Similarity	NPC474922
0.7791	Intermediate Similarity	NPC102048
0.7791	Intermediate Similarity	NPC46320
0.7789	Intermediate Similarity	NPC258547
0.7789	Intermediate Similarity	NPC283343
0.7789	Intermediate Similarity	NPC273668
0.7778	Intermediate Similarity	NPC72845
0.7778	Intermediate Similarity	NPC473944
0.7778	Intermediate Similarity	NPC472811
0.7766	Intermediate Similarity	NPC228251
0.7766	Intermediate Similarity	NPC477968
0.7766	Intermediate Similarity	NPC219285
0.7766	Intermediate Similarity	NPC472187
0.7766	Intermediate Similarity	NPC473204
0.7766	Intermediate Similarity	NPC477972
0.7766	Intermediate Similarity	NPC20113
0.7766	Intermediate Similarity	NPC473545
0.7766	Intermediate Similarity	NPC161527
0.7766	Intermediate Similarity	NPC477971
0.7765	Intermediate Similarity	NPC471408
0.7765	Intermediate Similarity	NPC2524
0.7753	Intermediate Similarity	NPC73995
0.7753	Intermediate Similarity	NPC284561
0.7753	Intermediate Similarity	NPC314727
0.7753	Intermediate Similarity	NPC16265
0.775	Intermediate Similarity	NPC16349
0.775	Intermediate Similarity	NPC222244
0.7742	Intermediate Similarity	NPC110937
0.7742	Intermediate Similarity	NPC285513
0.7742	Intermediate Similarity	NPC254496
0.7738	Intermediate Similarity	NPC281880
0.7738	Intermediate Similarity	NPC195424
0.7738	Intermediate Similarity	NPC268827
0.7732	Intermediate Similarity	NPC88349
0.7727	Intermediate Similarity	NPC162107
0.7727	Intermediate Similarity	NPC478104
0.7727	Intermediate Similarity	NPC473891
0.7727	Intermediate Similarity	NPC46912
0.7722	Intermediate Similarity	NPC469660
0.7717	Intermediate Similarity	NPC37603
0.7717	Intermediate Similarity	NPC183012
0.7717	Intermediate Similarity	NPC471786
0.7717	Intermediate Similarity	NPC476519
0.7708	Intermediate Similarity	NPC473523
0.7701	Intermediate Similarity	NPC189311
0.7701	Intermediate Similarity	NPC109528
0.7701	Intermediate Similarity	NPC191965
0.7692	Intermediate Similarity	NPC38232
0.7692	Intermediate Similarity	NPC205034
0.7692	Intermediate Similarity	NPC152778
0.7692	Intermediate Similarity	NPC162615
0.7692	Intermediate Similarity	NPC472812
0.7692	Intermediate Similarity	NPC476945
0.7684	Intermediate Similarity	NPC303559
0.7674	Intermediate Similarity	NPC139206
0.7674	Intermediate Similarity	NPC474789
0.7674	Intermediate Similarity	NPC193198
0.7674	Intermediate Similarity	NPC52108
0.7674	Intermediate Similarity	NPC127917
0.7674	Intermediate Similarity	NPC42476
0.7667	Intermediate Similarity	NPC48732
0.7667	Intermediate Similarity	NPC310479
0.7667	Intermediate Similarity	NPC212679
0.7667	Intermediate Similarity	NPC273199
0.7667	Intermediate Similarity	NPC469595
0.7667	Intermediate Similarity	NPC474728
0.7667	Intermediate Similarity	NPC302280
0.7667	Intermediate Similarity	NPC220454
0.7667	Intermediate Similarity	NPC152467
0.766	Intermediate Similarity	NPC278386
0.766	Intermediate Similarity	NPC159763
0.766	Intermediate Similarity	NPC92275
0.766	Intermediate Similarity	NPC124512

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 NPC25554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1503
0.2-0.3	3946
0.3-0.4	2354
0.4-0.5	789
0.5-0.6	300
0.6-0.7	82
0.7-0.8	5
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
0.7753	Intermediate Similarity	NPD6051	Approved
0.766	Intermediate Similarity	NPD4225	Approved
0.7474	Intermediate Similarity	NPD7638	Approved
0.7396	Intermediate Similarity	NPD7640	Approved
0.7396	Intermediate Similarity	NPD7639	Approved
0.7356	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1694	Approved
0.7234	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7748	Approved
0.7234	Intermediate Similarity	NPD7900	Approved
0.7179	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8039	Approved
0.7128	Intermediate Similarity	NPD6399	Phase 3
0.7041	Intermediate Similarity	NPD6648	Approved
0.7033	Intermediate Similarity	NPD7521	Approved
0.7033	Intermediate Similarity	NPD6409	Approved
0.7033	Intermediate Similarity	NPD7334	Approved
0.7033	Intermediate Similarity	NPD5330	Approved
0.7033	Intermediate Similarity	NPD7146	Approved
0.7033	Intermediate Similarity	NPD6684	Approved
0.7021	Intermediate Similarity	NPD7515	Phase 2
0.7011	Intermediate Similarity	NPD7645	Phase 2
0.701	Intermediate Similarity	NPD7902	Approved
0.7009	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5344	Discontinued
0.6941	Remote Similarity	NPD8264	Approved
0.6882	Remote Similarity	NPD6903	Approved
0.6882	Remote Similarity	NPD5737	Approved
0.6882	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3573	Approved
0.6744	Remote Similarity	NPD6942	Approved
0.6744	Remote Similarity	NPD7339	Approved
0.6742	Remote Similarity	NPD7525	Registered
0.6733	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD7327	Approved
0.6636	Remote Similarity	NPD7328	Approved
0.6633	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4786	Approved
0.663	Remote Similarity	NPD3668	Phase 3
0.6607	Remote Similarity	NPD8033	Approved
0.6604	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5778	Approved
0.6598	Remote Similarity	NPD5779	Approved
0.6593	Remote Similarity	NPD3667	Approved
0.6577	Remote Similarity	NPD7516	Approved
0.6571	Remote Similarity	NPD6686	Approved
0.6562	Remote Similarity	NPD6698	Approved
0.6562	Remote Similarity	NPD46	Approved
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD6008	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6518	Remote Similarity	NPD8294	Approved
0.6518	Remote Similarity	NPD8377	Approved
0.6495	Remote Similarity	NPD8034	Phase 2
0.6495	Remote Similarity	NPD8035	Phase 2
0.6489	Remote Similarity	NPD6098	Approved
0.6489	Remote Similarity	NPD3618	Phase 1
0.6481	Remote Similarity	NPD8297	Approved
0.646	Remote Similarity	NPD8296	Approved
0.646	Remote Similarity	NPD8380	Approved
0.646	Remote Similarity	NPD8335	Approved
0.646	Remote Similarity	NPD8379	Approved
0.646	Remote Similarity	NPD7503	Approved
0.646	Remote Similarity	NPD8378	Approved
0.6458	Remote Similarity	NPD6673	Approved
0.6458	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6080	Approved
0.6458	Remote Similarity	NPD6101	Approved
0.6458	Remote Similarity	NPD6904	Approved
0.6458	Remote Similarity	NPD5328	Approved
0.6421	Remote Similarity	NPD7524	Approved
0.6415	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD6881	Approved
0.6413	Remote Similarity	NPD5209	Approved
0.64	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7838	Discovery
0.6383	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6373	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6344	Remote Similarity	NPD6695	Phase 3
0.6337	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD6083	Phase 2
0.6327	Remote Similarity	NPD6050	Approved
0.6327	Remote Similarity	NPD6079	Approved
0.6321	Remote Similarity	NPD5697	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6311	Remote Similarity	NPD4159	Approved
0.63	Remote Similarity	NPD5695	Phase 3
0.6296	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD7102	Approved
0.6292	Remote Similarity	NPD6933	Approved
0.6277	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD6924	Approved
0.625	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6926	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD7507	Approved
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6224	Remote Similarity	NPD5692	Phase 3
0.6224	Remote Similarity	NPD5785	Approved
0.6207	Remote Similarity	NPD7152	Approved
0.6207	Remote Similarity	NPD7150	Approved
0.6207	Remote Similarity	NPD7151	Approved
0.6204	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6013	Approved
0.6204	Remote Similarity	NPD6014	Approved
0.6204	Remote Similarity	NPD6012	Approved
0.62	Remote Similarity	NPD6001	Approved
0.6196	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5208	Approved
0.6182	Remote Similarity	NPD6882	Approved
0.617	Remote Similarity	NPD7154	Phase 3
0.617	Remote Similarity	NPD5362	Discontinued
0.6163	Remote Similarity	NPD6922	Approved
0.6163	Remote Similarity	NPD6923	Approved
0.6162	Remote Similarity	NPD5694	Approved
0.6154	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6422	Discontinued
0.6126	Remote Similarity	NPD4632	Approved
0.6122	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5696	Approved
0.6105	Remote Similarity	NPD3666	Approved
0.6105	Remote Similarity	NPD3133	Approved
0.6105	Remote Similarity	NPD3665	Phase 1
0.61	Remote Similarity	NPD4202	Approved
0.6098	Remote Similarity	NPD368	Approved
0.6092	Remote Similarity	NPD7143	Approved
0.6092	Remote Similarity	NPD7144	Approved
0.6087	Remote Similarity	NPD6929	Approved
0.6083	Remote Similarity	NPD7319	Approved
0.6082	Remote Similarity	NPD7750	Discontinued
0.6078	Remote Similarity	NPD5221	Approved
0.6078	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5222	Approved
0.6078	Remote Similarity	NPD4697	Phase 3
0.6067	Remote Similarity	NPD4784	Approved
0.6067	Remote Similarity	NPD4785	Approved
0.6061	Remote Similarity	NPD5207	Approved
0.6061	Remote Similarity	NPD3168	Discontinued
0.6044	Remote Similarity	NPD5776	Phase 2
0.6044	Remote Similarity	NPD6925	Approved
0.6042	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6053	Discontinued
0.6034	Remote Similarity	NPD8516	Approved
0.6034	Remote Similarity	NPD8517	Approved
0.6034	Remote Similarity	NPD8515	Approved
0.6034	Remote Similarity	NPD8513	Phase 3
0.6023	Remote Similarity	NPD4243	Approved
0.6022	Remote Similarity	NPD6931	Approved
0.6022	Remote Similarity	NPD4822	Approved
0.6022	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4819	Approved
0.6022	Remote Similarity	NPD4821	Approved
0.6022	Remote Similarity	NPD4748	Discontinued
0.6022	Remote Similarity	NPD7514	Phase 3
0.6022	Remote Similarity	NPD4820	Approved
0.6022	Remote Similarity	NPD6930	Phase 2
0.6022	Remote Similarity	NPD7332	Phase 2
0.6022	Remote Similarity	NPD7509	Discontinued
0.6022	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD6412	Phase 2
0.6019	Remote Similarity	NPD5173	Approved
0.6018	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD7983	Approved
0.6	Remote Similarity	NPD5332	Approved
0.5982	Remote Similarity	NPD8133	Approved
0.5978	Remote Similarity	NPD4268	Approved
0.5978	Remote Similarity	NPD4271	Approved
0.5978	Remote Similarity	NPD7145	Approved
0.5976	Remote Similarity	NPD1145	Discontinued
0.5965	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6009	Approved
0.5957	Remote Similarity	NPD4790	Discontinued
0.5957	Remote Similarity	NPD6902	Approved
0.5948	Remote Similarity	NPD6319	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