NPASS Compound

Structure

NPC471610 OpenBabel07101718312D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.7315 -2.8880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1701 1.1740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5635 -2.1726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3060 1.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5326 1.3876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4232 -1.5829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0103 -1.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4225 -0.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7643 0.0792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0572 -0.6279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3226 -3.0696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3103 -3.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5494 -0.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7643 -2.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4225 -1.9370 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3265 0.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7248 -1.6279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1662 -2.0819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4714 -0.6279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7643 0.0792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4714 -1.6279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0572 -1.6279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6158 -0.0847 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7771 -0.6293 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2601 -0.1721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1470 1.0030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3584 0.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7643 -2.3351 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0373 0.4572 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4166 -1.1598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5382 1.7964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1384 1.1336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3570 0.8812 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 2 16 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 18 2 0 0 0 0 12 28 1 0 0 0 0 13 16 2 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 1 1 6 0 0 0 15 21 1 0 0 0 0 16 25 1 0 0 0 0 17 3 1 6 0 0 0 17 18 1 0 0 0 0 18 22 1 0 0 0 0 19 8 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 0 0 0 0 21 14 1 6 0 0 0 22 28 1 6 0 0 0 23 24 1 0 0 0 0 23 33 1 0 0 0 0 24 17 1 1 0 0 0 24 34 1 0 0 0 0 25 29 2 0 0 0 0 25 30 1 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 27 34 1 0 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.28
Volume:	498.177
LogP:	6.0
LogD:	4.64
LogS:	-3.64
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	5.381
Fsp3:	0.714
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:	-5.242
MDCK Permeability:	1.582586810400244e-05
Pgp-inhibitor:	0.341
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.467
20% Bioavailability (F20%):	0.416
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	95.1821060180664%
Volume Distribution (VD):	0.599
Pgp-substrate:	4.69175386428833%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.366
CYP2C9-inhibitor:	0.339
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	1.573
Half-life (T1/2):	0.475

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.76
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.385
Maximum Recommended Daily Dose:	0.513
Skin Sensitization:	0.923
Carcinogencity:	0.806
Eye Corrosion:	0.005
Eye Irritation:	0.087
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC471610

Natural Product ID:	NPC471610
*Common Name:**	KYAGGFDVLXQVAI-WNHGOZILSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KYAGGFDVLXQVAI-WNHGOZILSA-N
Standard InCHI:	InChI=1S/C28H40O6/c1-15-7-8-19-20(26(31)32)9-10-22-18(11-12-28(22,6)14-21(15)19)17(3)24-23(13-16(2)25(29)30)33-27(4,5)34-24/h9,11,13,15,17,19,21-24H,7-8,10,12,14H2,1-6H3,(H,29,30)(H,31,32)/b16-13+,20-9+/t15-,17-,19-,21-,22-,23?,24-,28+/m1/s1
SMILES:	CC1CCC2C1CC3(CC=C(C3CC=C2C(=O)O)C(C)C4C(OC(O4)(C)C)C=C(C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL293560
PubChem CID:	44302014
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002882] Ophiobolane sesterterpenoids

*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
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11454459]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21265556]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	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
MIC	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	19.0	ug.mL-1	PMID[510662]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	200.0	ug.mL-1	PMID[510662]

☑ 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 NPC471610 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	223
0.1-0.2	1239
0.2-0.3	5036
0.3-0.4	13894
0.4-0.5	9975
0.5-0.6	7616
0.6-0.7	4061
0.7-0.8	634
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.871	High Similarity	NPC477215
0.871	High Similarity	NPC476388
0.8247	Intermediate Similarity	NPC37816
0.8137	Intermediate Similarity	NPC25639
0.798	Intermediate Similarity	NPC90453
0.7961	Intermediate Similarity	NPC86077
0.7959	Intermediate Similarity	NPC141831
0.79	Intermediate Similarity	NPC476487
0.79	Intermediate Similarity	NPC476488
0.7857	Intermediate Similarity	NPC49946
0.7857	Intermediate Similarity	NPC281942
0.7857	Intermediate Similarity	NPC232426
0.7857	Intermediate Similarity	NPC306168
0.78	Intermediate Similarity	NPC477131
0.78	Intermediate Similarity	NPC167219
0.7778	Intermediate Similarity	NPC290651
0.7755	Intermediate Similarity	NPC268298
0.7745	Intermediate Similarity	NPC476253
0.7736	Intermediate Similarity	NPC153095
0.7723	Intermediate Similarity	NPC472469
0.7717	Intermediate Similarity	NPC93763
0.7717	Intermediate Similarity	NPC108816
0.7714	Intermediate Similarity	NPC476237
0.7699	Intermediate Similarity	NPC474179
0.7699	Intermediate Similarity	NPC475834
0.7692	Intermediate Similarity	NPC195192
0.7692	Intermediate Similarity	NPC304738
0.7677	Intermediate Similarity	NPC474761
0.7677	Intermediate Similarity	NPC469368
0.7677	Intermediate Similarity	NPC476004
0.7677	Intermediate Similarity	NPC129419
0.767	Intermediate Similarity	NPC98868
0.767	Intermediate Similarity	NPC141191
0.767	Intermediate Similarity	NPC187268
0.766	Intermediate Similarity	NPC325031
0.7653	Intermediate Similarity	NPC472378
0.7647	Intermediate Similarity	NPC470801
0.7629	Intermediate Similarity	NPC305475
0.7629	Intermediate Similarity	NPC475461
0.7629	Intermediate Similarity	NPC107787
0.7624	Intermediate Similarity	NPC470013
0.7624	Intermediate Similarity	NPC474338
0.7624	Intermediate Similarity	NPC323008
0.7624	Intermediate Similarity	NPC53685
0.7624	Intermediate Similarity	NPC96541
0.7624	Intermediate Similarity	NPC198853
0.7624	Intermediate Similarity	NPC262133
0.7624	Intermediate Similarity	NPC470010
0.7611	Intermediate Similarity	NPC475913
0.7604	Intermediate Similarity	NPC82297
0.7604	Intermediate Similarity	NPC238197
0.76	Intermediate Similarity	NPC300312
0.76	Intermediate Similarity	NPC261607
0.76	Intermediate Similarity	NPC111114
0.76	Intermediate Similarity	NPC133698
0.76	Intermediate Similarity	NPC221282
0.7596	Intermediate Similarity	NPC476303
0.7596	Intermediate Similarity	NPC469872
0.7596	Intermediate Similarity	NPC469864
0.7593	Intermediate Similarity	NPC220155
0.7579	Intermediate Similarity	NPC35556
0.7576	Intermediate Similarity	NPC295312
0.7576	Intermediate Similarity	NPC212664
0.7576	Intermediate Similarity	NPC288699
0.7576	Intermediate Similarity	NPC232747
0.7573	Intermediate Similarity	NPC169205
0.7573	Intermediate Similarity	NPC202705
0.757	Intermediate Similarity	NPC243998
0.757	Intermediate Similarity	NPC223450
0.7553	Intermediate Similarity	NPC276356
0.7551	Intermediate Similarity	NPC312561
0.7551	Intermediate Similarity	NPC160138
0.7551	Intermediate Similarity	NPC237540
0.7549	Intermediate Similarity	NPC293052
0.7549	Intermediate Similarity	NPC67584
0.7549	Intermediate Similarity	NPC304886
0.7547	Intermediate Similarity	NPC176883
0.7545	Intermediate Similarity	NPC474750
0.7526	Intermediate Similarity	NPC78089
0.7526	Intermediate Similarity	NPC255307
0.7525	Intermediate Similarity	NPC156553
0.7525	Intermediate Similarity	NPC229976
0.7525	Intermediate Similarity	NPC469692
0.7525	Intermediate Similarity	NPC469645
0.7525	Intermediate Similarity	NPC472871
0.7524	Intermediate Similarity	NPC150923
0.75	Intermediate Similarity	NPC475622
0.75	Intermediate Similarity	NPC108045
0.75	Intermediate Similarity	NPC51004
0.75	Intermediate Similarity	NPC301969
0.75	Intermediate Similarity	NPC474181
0.75	Intermediate Similarity	NPC65350
0.75	Intermediate Similarity	NPC37607
0.75	Intermediate Similarity	NPC475947
0.75	Intermediate Similarity	NPC475995
0.75	Intermediate Similarity	NPC473448
0.75	Intermediate Similarity	NPC475176
0.75	Intermediate Similarity	NPC474098
0.7477	Intermediate Similarity	NPC474917
0.7477	Intermediate Similarity	NPC203659
0.7476	Intermediate Similarity	NPC185553
0.7476	Intermediate Similarity	NPC213078
0.7476	Intermediate Similarity	NPC18019
0.7476	Intermediate Similarity	NPC24956
0.7475	Intermediate Similarity	NPC472870
0.7475	Intermediate Similarity	NPC91248
0.7455	Intermediate Similarity	NPC37116
0.7455	Intermediate Similarity	NPC29133
0.7453	Intermediate Similarity	NPC475320
0.7451	Intermediate Similarity	NPC121825
0.7449	Intermediate Similarity	NPC474045
0.7449	Intermediate Similarity	NPC469483
0.7449	Intermediate Similarity	NPC261253
0.7447	Intermediate Similarity	NPC469620
0.7447	Intermediate Similarity	NPC469690
0.7447	Intermediate Similarity	NPC182550
0.7431	Intermediate Similarity	NPC475960
0.7429	Intermediate Similarity	NPC241221
0.7429	Intermediate Similarity	NPC201406
0.7426	Intermediate Similarity	NPC303697
0.7426	Intermediate Similarity	NPC165904
0.7426	Intermediate Similarity	NPC179517
0.7426	Intermediate Similarity	NPC131209
0.7426	Intermediate Similarity	NPC470113
0.7426	Intermediate Similarity	NPC30515
0.7426	Intermediate Similarity	NPC477783
0.7426	Intermediate Similarity	NPC475925
0.7426	Intermediate Similarity	NPC473707
0.7426	Intermediate Similarity	NPC190442
0.7423	Intermediate Similarity	NPC115786
0.7423	Intermediate Similarity	NPC114979
0.7423	Intermediate Similarity	NPC156485
0.7423	Intermediate Similarity	NPC476804
0.7423	Intermediate Similarity	NPC475100
0.7423	Intermediate Similarity	NPC191476
0.7419	Intermediate Similarity	NPC116177
0.7419	Intermediate Similarity	NPC320630
0.7419	Intermediate Similarity	NPC7563
0.7407	Intermediate Similarity	NPC475414
0.7407	Intermediate Similarity	NPC472751
0.7407	Intermediate Similarity	NPC173172
0.7407	Intermediate Similarity	NPC472749
0.7407	Intermediate Similarity	NPC127609
0.7407	Intermediate Similarity	NPC475217
0.7407	Intermediate Similarity	NPC127790
0.7404	Intermediate Similarity	NPC108475
0.7404	Intermediate Similarity	NPC475709
0.7404	Intermediate Similarity	NPC161493
0.7404	Intermediate Similarity	NPC253826
0.7404	Intermediate Similarity	NPC474343
0.7404	Intermediate Similarity	NPC477949
0.7404	Intermediate Similarity	NPC213947
0.7404	Intermediate Similarity	NPC170143
0.74	Intermediate Similarity	NPC139418
0.74	Intermediate Similarity	NPC83423
0.74	Intermediate Similarity	NPC474032
0.74	Intermediate Similarity	NPC307411
0.7396	Intermediate Similarity	NPC474291
0.7396	Intermediate Similarity	NPC471296
0.7387	Intermediate Similarity	NPC470961
0.7383	Intermediate Similarity	NPC472747
0.7383	Intermediate Similarity	NPC110989
0.7383	Intermediate Similarity	NPC180204
0.7383	Intermediate Similarity	NPC472750
0.7383	Intermediate Similarity	NPC112009
0.7383	Intermediate Similarity	NPC472755
0.7379	Intermediate Similarity	NPC36954
0.7379	Intermediate Similarity	NPC33473
0.7379	Intermediate Similarity	NPC90121
0.7379	Intermediate Similarity	NPC52044
0.7379	Intermediate Similarity	NPC193645
0.7379	Intermediate Similarity	NPC48803
0.7379	Intermediate Similarity	NPC275960
0.7379	Intermediate Similarity	NPC471141
0.7374	Intermediate Similarity	NPC45957
0.7374	Intermediate Similarity	NPC72513
0.7374	Intermediate Similarity	NPC167877
0.7374	Intermediate Similarity	NPC471657
0.7368	Intermediate Similarity	NPC74673
0.7368	Intermediate Similarity	NPC302426
0.7368	Intermediate Similarity	NPC284068
0.7368	Intermediate Similarity	NPC473656
0.7368	Intermediate Similarity	NPC475323
0.7368	Intermediate Similarity	NPC69271
0.7364	Intermediate Similarity	NPC47951
0.7358	Intermediate Similarity	NPC146822
0.7358	Intermediate Similarity	NPC118174
0.7358	Intermediate Similarity	NPC303559
0.7358	Intermediate Similarity	NPC99411
0.7353	Intermediate Similarity	NPC475912
0.7353	Intermediate Similarity	NPC135776
0.7353	Intermediate Similarity	NPC476300
0.7353	Intermediate Similarity	NPC179746
0.7353	Intermediate Similarity	NPC81419
0.7347	Intermediate Similarity	NPC474694
0.7347	Intermediate Similarity	NPC125290
0.7347	Intermediate Similarity	NPC161957
0.7347	Intermediate Similarity	NPC21471
0.7347	Intermediate Similarity	NPC473659
0.7347	Intermediate Similarity	NPC165162

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 NPC471610 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1863
0.2-0.3	3832
0.3-0.4	2281
0.4-0.5	573
0.5-0.6	307
0.6-0.7	80
0.7-0.8	9
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
0.7684	Intermediate Similarity	NPD5362	Discontinued
0.7677	Intermediate Similarity	NPD5785	Approved
0.7379	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6371	Approved
0.7273	Intermediate Similarity	NPD6686	Approved
0.7172	Intermediate Similarity	NPD5363	Approved
0.717	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD7154	Phase 3
0.7113	Intermediate Similarity	NPD4790	Discontinued
0.7069	Intermediate Similarity	NPD7115	Discovery
0.7041	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6698	Approved
0.699	Remote Similarity	NPD46	Approved
0.697	Remote Similarity	NPD5332	Approved
0.697	Remote Similarity	NPD5331	Approved
0.6944	Remote Similarity	NPD7640	Approved
0.6944	Remote Similarity	NPD7639	Approved
0.6893	Remote Similarity	NPD1695	Approved
0.6869	Remote Similarity	NPD4269	Approved
0.6869	Remote Similarity	NPD4270	Approved
0.6857	Remote Similarity	NPD6399	Phase 3
0.6852	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7638	Approved
0.6837	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1694	Approved
0.6765	Remote Similarity	NPD5786	Approved
0.6748	Remote Similarity	NPD7507	Approved
0.6733	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5209	Approved
0.6699	Remote Similarity	NPD4251	Approved
0.6699	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6638	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5737	Approved
0.6635	Remote Similarity	NPD6903	Approved
0.6635	Remote Similarity	NPD6672	Approved
0.6633	Remote Similarity	NPD4268	Approved
0.6633	Remote Similarity	NPD4271	Approved
0.6606	Remote Similarity	NPD6084	Phase 2
0.6606	Remote Similarity	NPD6083	Phase 2
0.6604	Remote Similarity	NPD7637	Suspended
0.6602	Remote Similarity	NPD7334	Approved
0.6602	Remote Similarity	NPD5330	Approved
0.6602	Remote Similarity	NPD7146	Approved
0.6602	Remote Similarity	NPD6409	Approved
0.6602	Remote Similarity	NPD4249	Approved
0.6602	Remote Similarity	NPD6684	Approved
0.6602	Remote Similarity	NPD7521	Approved
0.66	Remote Similarity	NPD5369	Approved
0.6587	Remote Similarity	NPD7319	Approved
0.6581	Remote Similarity	NPD6882	Approved
0.6581	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5695	Phase 3
0.656	Remote Similarity	NPD7078	Approved
0.6535	Remote Similarity	NPD6435	Approved
0.6532	Remote Similarity	NPD7492	Approved
0.6505	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5282	Discontinued
0.648	Remote Similarity	NPD6616	Approved
0.6476	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6054	Approved
0.6449	Remote Similarity	NPD5693	Phase 1
0.6449	Remote Similarity	NPD7983	Approved
0.6446	Remote Similarity	NPD7328	Approved
0.6446	Remote Similarity	NPD7327	Approved
0.6441	Remote Similarity	NPD8297	Approved
0.6423	Remote Similarity	NPD8033	Approved
0.6422	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4786	Approved
0.6396	Remote Similarity	NPD5696	Approved
0.6393	Remote Similarity	NPD7516	Approved
0.6389	Remote Similarity	NPD5779	Approved
0.6389	Remote Similarity	NPD5778	Approved
0.6379	Remote Similarity	NPD6881	Approved
0.6379	Remote Similarity	NPD6899	Approved
0.6379	Remote Similarity	NPD7320	Approved
0.6378	Remote Similarity	NPD7736	Approved
0.6372	Remote Similarity	NPD7632	Discontinued
0.6371	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD6009	Approved
0.6348	Remote Similarity	NPD6675	Approved
0.6348	Remote Similarity	NPD6402	Approved
0.6348	Remote Similarity	NPD7128	Approved
0.6348	Remote Similarity	NPD5739	Approved
0.6341	Remote Similarity	NPD8377	Approved
0.6341	Remote Similarity	NPD6059	Approved
0.6341	Remote Similarity	NPD8294	Approved
0.6337	Remote Similarity	NPD5368	Approved
0.633	Remote Similarity	NPD7748	Approved
0.6327	Remote Similarity	NPD8039	Approved
0.6299	Remote Similarity	NPD8293	Discontinued
0.6296	Remote Similarity	NPD6411	Approved
0.6296	Remote Similarity	NPD6079	Approved
0.6293	Remote Similarity	NPD5697	Approved
0.629	Remote Similarity	NPD8379	Approved
0.629	Remote Similarity	NPD8335	Approved
0.629	Remote Similarity	NPD6016	Approved
0.629	Remote Similarity	NPD8380	Approved
0.629	Remote Similarity	NPD7503	Approved
0.629	Remote Similarity	NPD8296	Approved
0.629	Remote Similarity	NPD6015	Approved
0.629	Remote Similarity	NPD8378	Approved
0.6286	Remote Similarity	NPD5279	Phase 3
0.6283	Remote Similarity	NPD5344	Discontinued
0.6271	Remote Similarity	NPD7102	Approved
0.6271	Remote Similarity	NPD7290	Approved
0.6271	Remote Similarity	NPD6883	Approved
0.6262	Remote Similarity	NPD6673	Approved
0.6262	Remote Similarity	NPD5328	Approved
0.6262	Remote Similarity	NPD6080	Approved
0.6262	Remote Similarity	NPD6904	Approved
0.6262	Remote Similarity	NPD6051	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3666	Approved
0.624	Remote Similarity	NPD5988	Approved
0.6239	Remote Similarity	NPD6011	Approved
0.6226	Remote Similarity	NPD7524	Approved
0.6218	Remote Similarity	NPD6649	Approved
0.6218	Remote Similarity	NPD6869	Approved
0.6218	Remote Similarity	NPD6617	Approved
0.6218	Remote Similarity	NPD6847	Approved
0.6218	Remote Similarity	NPD6650	Approved
0.6218	Remote Similarity	NPD8130	Phase 1
0.6216	Remote Similarity	NPD7839	Suspended
0.6214	Remote Similarity	NPD3667	Approved
0.6207	Remote Similarity	NPD6008	Approved
0.6204	Remote Similarity	NPD5207	Approved
0.6195	Remote Similarity	NPD6648	Approved
0.6195	Remote Similarity	NPD6404	Discontinued
0.619	Remote Similarity	NPD7122	Discontinued
0.6186	Remote Similarity	NPD6372	Approved
0.6186	Remote Similarity	NPD6013	Approved
0.6186	Remote Similarity	NPD6014	Approved
0.6186	Remote Similarity	NPD6012	Approved
0.6186	Remote Similarity	NPD6373	Approved
0.6161	Remote Similarity	NPD7902	Approved
0.616	Remote Similarity	NPD8516	Approved
0.616	Remote Similarity	NPD8515	Approved
0.616	Remote Similarity	NPD8517	Approved
0.616	Remote Similarity	NPD8513	Phase 3
0.6154	Remote Similarity	NPD6695	Phase 3
0.6154	Remote Similarity	NPD5701	Approved
0.6147	Remote Similarity	NPD8034	Phase 2
0.6147	Remote Similarity	NPD5281	Approved
0.6147	Remote Similarity	NPD7515	Phase 2
0.6147	Remote Similarity	NPD8035	Phase 2
0.6147	Remote Similarity	NPD5284	Approved
0.6147	Remote Similarity	NPD6050	Approved
0.6132	Remote Similarity	NPD3618	Phase 1
0.6116	Remote Similarity	NPD8133	Approved
0.6116	Remote Similarity	NPD4632	Approved
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4753	Phase 2
0.6111	Remote Similarity	NPD6101	Approved
0.6107	Remote Similarity	NPD7260	Phase 2
0.6095	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5211	Phase 2
0.6083	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5221	Approved
0.6071	Remote Similarity	NPD5222	Approved
0.6064	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6067	Discontinued
0.6061	Remote Similarity	NPD6845	Suspended
0.6058	Remote Similarity	NPD4221	Approved
0.6058	Remote Similarity	NPD4223	Phase 3
0.6055	Remote Similarity	NPD5692	Phase 3
0.605	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4756	Discovery
0.6038	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5329	Approved
0.6036	Remote Similarity	NPD6001	Approved
0.6019	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD5208	Approved
0.6018	Remote Similarity	NPD5173	Approved
0.6016	Remote Similarity	NPD6868	Approved
0.6015	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5694	Approved
0.5983	Remote Similarity	NPD5141	Approved
0.5982	Remote Similarity	NPD5210	Approved
0.5982	Remote Similarity	NPD4629	Approved
0.5981	Remote Similarity	NPD4519	Discontinued
0.5981	Remote Similarity	NPD5690	Phase 2
0.5981	Remote Similarity	NPD4623	Approved
0.5981	Remote Similarity	NPD6098	Approved
0.5963	Remote Similarity	NPD5370	Suspended

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