NPASS Compound

Structure

CID273269 OpenBabel06191716082D 29 30 0 0 1 0 0 0 0 0999 V2000 -5.0285 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3542 -2.2897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0285 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1904 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3524 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3220 -3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8058 -4.8040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3524 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -1.4516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3524 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5143 -1.4516 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8058 -3.1278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 -0.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5143 0.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8381 0.4839 0.0000 C 0 0 0 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 0.8381 -1.4516 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7736 -4.8040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5143 -2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7736 -3.1278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5143 1.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 1.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 0.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 2 1 6 0 0 0 13 18 1 0 0 0 0 14 3 1 6 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 25 1 6 0 0 0 16 23 1 0 0 0 0 16 26 2 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 6 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 23 1 1 0 0 0 20 27 1 6 0 0 0 21 22 1 0 0 0 0 21 28 2 0 0 0 0 22 29 1 0 0 0 0 23 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.25
Volume:	431.447
LogP:	2.512
LogD:	2.401
LogS:	-3.949
# Rotatable Bonds:	9
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	4.941
Fsp3:	0.826
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.722
MDCK Permeability:	3.801171260420233e-05
Pgp-inhibitor:	0.815
Pgp-substrate:	0.56
Human Intestinal Absorption (HIA):	0.646
20% Bioavailability (F20%):	0.35
30% Bioavailability (F30%):	0.603

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.828
Plasma Protein Binding (PPB):	68.37818145751953%
Volume Distribution (VD):	0.74
Pgp-substrate:	23.963232040405273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.529
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.737
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	9.61
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.264
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.745
Maximum Recommended Daily Dose:	0.09
Skin Sensitization:	0.516
Carcinogencity:	0.085
Eye Corrosion:	0.027
Eye Irritation:	0.033
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC273269

Natural Product ID:	NPC273269
*Common Name:**	Australifungin
IUPAC Name:	(4S,4aR,5S,7R,8R,8aS)-2,5,8-trihydroxy-4-[(Z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(2R)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1-one
Synonyms:	Australifungin
Standard InCHIKey:	QURROFPXYUFYAZ-GFHGMWMXSA-N
Standard InCHI:	InChI=1S/C23H36O6/c1-5-6-7-8-9-13(2)18-22(29)21(28)17-19(15(25)12-14(3)20(17)27)23(18,4)16(26)10-11-24/h10-11,13-15,17,19-20,24-25,27,29H,5-9,12H2,1-4H3/b11-10-/t13-,14-,15+,17+,19-,20-,23-/m1/s1
SMILES:	CCCCCC[C@@H](C)C1=C(C(=O)[C@H]2[C@@H]([C@H](C[C@@H](C)[C@H]2O)O)[C@]1(C)C(=O)/C=CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512638
PubChem CID:	5276375
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32659	cytospora sp.	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713414]
NPO30212	Sporormiella australis	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7797434]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	20000.0	nM	PMID[559025]

☑ 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 NPC273269 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	205
0.1-0.2	1406
0.2-0.3	5317
0.3-0.4	9184
0.4-0.5	13550
0.5-0.6	7791
0.6-0.7	4421
0.7-0.8	812
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC46761
0.8485	Intermediate Similarity	NPC470184
0.8438	Intermediate Similarity	NPC103527
0.8317	Intermediate Similarity	NPC320294
0.8283	Intermediate Similarity	NPC147954
0.828	Intermediate Similarity	NPC229717
0.8182	Intermediate Similarity	NPC472690
0.8182	Intermediate Similarity	NPC472689
0.8182	Intermediate Similarity	NPC477267
0.8182	Intermediate Similarity	NPC477268
0.8155	Intermediate Similarity	NPC85529
0.8155	Intermediate Similarity	NPC32006
0.8113	Intermediate Similarity	NPC472928
0.8081	Intermediate Similarity	NPC5532
0.8081	Intermediate Similarity	NPC469545
0.8081	Intermediate Similarity	NPC61369
0.8077	Intermediate Similarity	NPC58370
0.8077	Intermediate Similarity	NPC43285
0.8061	Intermediate Similarity	NPC471207
0.8056	Intermediate Similarity	NPC247069
0.8041	Intermediate Similarity	NPC99380
0.802	Intermediate Similarity	NPC474720
0.8	Intermediate Similarity	NPC298904
0.798	Intermediate Similarity	NPC476245
0.798	Intermediate Similarity	NPC280725
0.7963	Intermediate Similarity	NPC198539
0.7961	Intermediate Similarity	NPC230918
0.7961	Intermediate Similarity	NPC275583
0.7959	Intermediate Similarity	NPC474807
0.7938	Intermediate Similarity	NPC134321
0.7938	Intermediate Similarity	NPC128672
0.7935	Intermediate Similarity	NPC189237
0.7925	Intermediate Similarity	NPC250018
0.7925	Intermediate Similarity	NPC470257
0.7925	Intermediate Similarity	NPC20192
0.7917	Intermediate Similarity	NPC471793
0.7917	Intermediate Similarity	NPC471791
0.7905	Intermediate Similarity	NPC472925
0.7879	Intermediate Similarity	NPC196227
0.7879	Intermediate Similarity	NPC258674
0.7879	Intermediate Similarity	NPC23170
0.7879	Intermediate Similarity	NPC196485
0.7879	Intermediate Similarity	NPC245972
0.7872	Intermediate Similarity	NPC470812
0.7872	Intermediate Similarity	NPC251170
0.787	Intermediate Similarity	NPC205534
0.7864	Intermediate Similarity	NPC163249
0.7864	Intermediate Similarity	NPC272472
0.7857	Intermediate Similarity	NPC185936
0.7857	Intermediate Similarity	NPC172101
0.7857	Intermediate Similarity	NPC168027
0.7857	Intermediate Similarity	NPC73457
0.785	Intermediate Similarity	NPC235077
0.7849	Intermediate Similarity	NPC103486
0.7843	Intermediate Similarity	NPC144956
0.7835	Intermediate Similarity	NPC472983
0.7835	Intermediate Similarity	NPC475108
0.7822	Intermediate Similarity	NPC473161
0.7822	Intermediate Similarity	NPC27105
0.7812	Intermediate Similarity	NPC220930
0.7812	Intermediate Similarity	NPC472324
0.7812	Intermediate Similarity	NPC272039
0.78	Intermediate Similarity	NPC272617
0.78	Intermediate Similarity	NPC474602
0.7789	Intermediate Similarity	NPC79573
0.7788	Intermediate Similarity	NPC251017
0.7788	Intermediate Similarity	NPC117185
0.7778	Intermediate Similarity	NPC477436
0.7778	Intermediate Similarity	NPC211230
0.7778	Intermediate Similarity	NPC477435
0.7778	Intermediate Similarity	NPC34315
0.7768	Intermediate Similarity	NPC268958
0.7767	Intermediate Similarity	NPC472924
0.7767	Intermediate Similarity	NPC115862
0.7766	Intermediate Similarity	NPC64600
0.7757	Intermediate Similarity	NPC300026
0.7757	Intermediate Similarity	NPC470615
0.7757	Intermediate Similarity	NPC27814
0.7755	Intermediate Similarity	NPC472325
0.7755	Intermediate Similarity	NPC230332
0.7748	Intermediate Similarity	NPC472927
0.7745	Intermediate Similarity	NPC471331
0.7745	Intermediate Similarity	NPC471330
0.7745	Intermediate Similarity	NPC472730
0.7745	Intermediate Similarity	NPC177680
0.7745	Intermediate Similarity	NPC203388
0.7745	Intermediate Similarity	NPC114274
0.7745	Intermediate Similarity	NPC472687
0.7745	Intermediate Similarity	NPC472729
0.7745	Intermediate Similarity	NPC99657
0.7745	Intermediate Similarity	NPC153776
0.7742	Intermediate Similarity	NPC44963
0.7742	Intermediate Similarity	NPC116797
0.7742	Intermediate Similarity	NPC472684
0.7736	Intermediate Similarity	NPC185
0.7732	Intermediate Similarity	NPC158778
0.7732	Intermediate Similarity	NPC58271
0.7723	Intermediate Similarity	NPC192428
0.7723	Intermediate Similarity	NPC165616
0.7723	Intermediate Similarity	NPC49371
0.7714	Intermediate Similarity	NPC213366
0.7714	Intermediate Similarity	NPC96268
0.7708	Intermediate Similarity	NPC94666
0.7708	Intermediate Similarity	NPC194417
0.7708	Intermediate Similarity	NPC158393
0.7706	Intermediate Similarity	NPC90769
0.7706	Intermediate Similarity	NPC71348
0.77	Intermediate Similarity	NPC111015
0.77	Intermediate Similarity	NPC302008
0.77	Intermediate Similarity	NPC474328
0.77	Intermediate Similarity	NPC478089
0.77	Intermediate Similarity	NPC191094
0.77	Intermediate Similarity	NPC212812
0.7692	Intermediate Similarity	NPC293753
0.7692	Intermediate Similarity	NPC197659
0.7677	Intermediate Similarity	NPC472978
0.7677	Intermediate Similarity	NPC116726
0.767	Intermediate Similarity	NPC287833
0.767	Intermediate Similarity	NPC15390
0.767	Intermediate Similarity	NPC55503
0.767	Intermediate Similarity	NPC156324
0.767	Intermediate Similarity	NPC88198
0.767	Intermediate Similarity	NPC157787
0.767	Intermediate Similarity	NPC472727
0.767	Intermediate Similarity	NPC472972
0.767	Intermediate Similarity	NPC472728
0.7664	Intermediate Similarity	NPC476802
0.7664	Intermediate Similarity	NPC295244
0.7664	Intermediate Similarity	NPC89171
0.7664	Intermediate Similarity	NPC168883
0.766	Intermediate Similarity	NPC48362
0.7653	Intermediate Similarity	NPC86319
0.7653	Intermediate Similarity	NPC69627
0.7653	Intermediate Similarity	NPC472973
0.7653	Intermediate Similarity	NPC275740
0.7653	Intermediate Similarity	NPC184663
0.7647	Intermediate Similarity	NPC43747
0.7647	Intermediate Similarity	NPC108078
0.7647	Intermediate Similarity	NPC18509
0.7642	Intermediate Similarity	NPC471333
0.7642	Intermediate Similarity	NPC128828
0.7642	Intermediate Similarity	NPC51452
0.7642	Intermediate Similarity	NPC181357
0.7642	Intermediate Similarity	NPC471332
0.7642	Intermediate Similarity	NPC166607
0.7636	Intermediate Similarity	NPC326264
0.7634	Intermediate Similarity	NPC172013
0.7624	Intermediate Similarity	NPC477438
0.7624	Intermediate Similarity	NPC477437
0.7624	Intermediate Similarity	NPC231060
0.7624	Intermediate Similarity	NPC84018
0.7624	Intermediate Similarity	NPC139570
0.7624	Intermediate Similarity	NPC297199
0.7624	Intermediate Similarity	NPC138245
0.7624	Intermediate Similarity	NPC255809
0.7624	Intermediate Similarity	NPC472485
0.7619	Intermediate Similarity	NPC111323
0.7619	Intermediate Similarity	NPC311612
0.7619	Intermediate Similarity	NPC249187
0.7619	Intermediate Similarity	NPC282233
0.7619	Intermediate Similarity	NPC159442
0.7619	Intermediate Similarity	NPC247957
0.7619	Intermediate Similarity	NPC95585
0.7619	Intermediate Similarity	NPC131366
0.7619	Intermediate Similarity	NPC239716
0.7615	Intermediate Similarity	NPC171888
0.7615	Intermediate Similarity	NPC146945
0.7611	Intermediate Similarity	NPC472933
0.7611	Intermediate Similarity	NPC470777
0.7604	Intermediate Similarity	NPC476426
0.76	Intermediate Similarity	NPC131840
0.7596	Intermediate Similarity	NPC476240
0.7596	Intermediate Similarity	NPC112613
0.7596	Intermediate Similarity	NPC224720
0.7596	Intermediate Similarity	NPC476223
0.7596	Intermediate Similarity	NPC60947
0.7593	Intermediate Similarity	NPC87335
0.7593	Intermediate Similarity	NPC258543
0.7593	Intermediate Similarity	NPC241927
0.7576	Intermediate Similarity	NPC80401
0.7576	Intermediate Similarity	NPC113393
0.7573	Intermediate Similarity	NPC288
0.7573	Intermediate Similarity	NPC103051
0.7573	Intermediate Similarity	NPC109059
0.757	Intermediate Similarity	NPC165873
0.757	Intermediate Similarity	NPC202524
0.757	Intermediate Similarity	NPC3316
0.757	Intermediate Similarity	NPC144854
0.7568	Intermediate Similarity	NPC238667
0.7568	Intermediate Similarity	NPC261330
0.7553	Intermediate Similarity	NPC55869
0.7551	Intermediate Similarity	NPC474854
0.7551	Intermediate Similarity	NPC307298
0.7551	Intermediate Similarity	NPC328539
0.7551	Intermediate Similarity	NPC472802
0.7551	Intermediate Similarity	NPC473229
0.7551	Intermediate Similarity	NPC53911
0.7551	Intermediate Similarity	NPC131470
0.7551	Intermediate Similarity	NPC143767
0.7551	Intermediate Similarity	NPC476796

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 NPC273269 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1915
0.2-0.3	3909
0.3-0.4	2081
0.4-0.5	661
0.5-0.6	197
0.6-0.7	150
0.7-0.8	49
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
0.79	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD5222	Approved
0.79	Intermediate Similarity	NPD5221	Approved
0.7857	Intermediate Similarity	NPD6079	Approved
0.785	Intermediate Similarity	NPD4634	Approved
0.7843	Intermediate Similarity	NPD5285	Approved
0.7843	Intermediate Similarity	NPD4696	Approved
0.7843	Intermediate Similarity	NPD5286	Approved
0.7822	Intermediate Similarity	NPD5173	Approved
0.7767	Intermediate Similarity	NPD5223	Approved
0.7723	Intermediate Similarity	NPD4697	Phase 3
0.7692	Intermediate Similarity	NPD5224	Approved
0.7692	Intermediate Similarity	NPD5211	Phase 2
0.7692	Intermediate Similarity	NPD4633	Approved
0.7692	Intermediate Similarity	NPD5226	Approved
0.7692	Intermediate Similarity	NPD5225	Approved
0.7653	Intermediate Similarity	NPD5328	Approved
0.7647	Intermediate Similarity	NPD4755	Approved
0.7624	Intermediate Similarity	NPD5210	Approved
0.7624	Intermediate Similarity	NPD4629	Approved
0.7619	Intermediate Similarity	NPD5174	Approved
0.7619	Intermediate Similarity	NPD5175	Approved
0.7547	Intermediate Similarity	NPD5141	Approved
0.7526	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.7455	Intermediate Similarity	NPD6649	Approved
0.7455	Intermediate Similarity	NPD6650	Approved
0.7447	Intermediate Similarity	NPD4695	Discontinued
0.7407	Intermediate Similarity	NPD5697	Approved
0.7391	Intermediate Similarity	NPD6054	Approved
0.7364	Intermediate Similarity	NPD7290	Approved
0.7364	Intermediate Similarity	NPD7102	Approved
0.7364	Intermediate Similarity	NPD6883	Approved
0.7339	Intermediate Similarity	NPD4729	Approved
0.7339	Intermediate Similarity	NPD4730	Approved
0.7339	Intermediate Similarity	NPD6011	Approved
0.7327	Intermediate Similarity	NPD7515	Phase 2
0.7321	Intermediate Similarity	NPD4632	Approved
0.7315	Intermediate Similarity	NPD6675	Approved
0.7315	Intermediate Similarity	NPD7128	Approved
0.7315	Intermediate Similarity	NPD5739	Approved
0.7315	Intermediate Similarity	NPD6402	Approved
0.7297	Intermediate Similarity	NPD6869	Approved
0.7297	Intermediate Similarity	NPD6617	Approved
0.7297	Intermediate Similarity	NPD8130	Phase 1
0.7297	Intermediate Similarity	NPD6847	Approved
0.729	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD6372	Approved
0.7265	Intermediate Similarity	NPD6370	Approved
0.7241	Intermediate Similarity	NPD6319	Approved
0.7232	Intermediate Similarity	NPD6882	Approved
0.7232	Intermediate Similarity	NPD8297	Approved
0.7207	Intermediate Similarity	NPD5247	Approved
0.7207	Intermediate Similarity	NPD5250	Approved
0.7207	Intermediate Similarity	NPD5169	Approved
0.7207	Intermediate Similarity	NPD5251	Approved
0.7207	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5249	Phase 3
0.7207	Intermediate Similarity	NPD5135	Approved
0.7207	Intermediate Similarity	NPD5248	Approved
0.7184	Intermediate Similarity	NPD5282	Discontinued
0.7182	Intermediate Similarity	NPD7320	Approved
0.7182	Intermediate Similarity	NPD5168	Approved
0.7182	Intermediate Similarity	NPD5128	Approved
0.7182	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6015	Approved
0.7179	Intermediate Similarity	NPD6016	Approved
0.7172	Intermediate Similarity	NPD5279	Phase 3
0.7156	Intermediate Similarity	NPD4767	Approved
0.7156	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3666	Approved
0.7143	Intermediate Similarity	NPD5216	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD5217	Approved
0.7143	Intermediate Similarity	NPD5215	Approved
0.713	Intermediate Similarity	NPD6009	Approved
0.7129	Intermediate Similarity	NPD4753	Phase 2
0.7119	Intermediate Similarity	NPD5988	Approved
0.7094	Intermediate Similarity	NPD6059	Approved
0.7091	Intermediate Similarity	NPD5701	Approved
0.7087	Intermediate Similarity	NPD4202	Approved
0.7083	Intermediate Similarity	NPD6616	Approved
0.7059	Intermediate Similarity	NPD8328	Phase 3
0.7053	Intermediate Similarity	NPD3617	Approved
0.7025	Intermediate Similarity	NPD7078	Approved
0.7019	Intermediate Similarity	NPD7748	Approved
0.7	Intermediate Similarity	NPD5690	Phase 2
0.6991	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6411	Approved
0.697	Remote Similarity	NPD4786	Approved
0.6967	Remote Similarity	NPD7736	Approved
0.6961	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5167	Approved
0.6939	Remote Similarity	NPD3667	Approved
0.6923	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD5779	Approved
0.6923	Remote Similarity	NPD5778	Approved
0.6917	Remote Similarity	NPD7604	Phase 2
0.6916	Remote Similarity	NPD5696	Approved
0.6907	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5329	Approved
0.6897	Remote Similarity	NPD6868	Approved
0.6891	Remote Similarity	NPD5983	Phase 2
0.6864	Remote Similarity	NPD7100	Approved
0.6864	Remote Similarity	NPD7101	Approved
0.6857	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7900	Approved
0.6838	Remote Similarity	NPD6317	Approved
0.6822	Remote Similarity	NPD6083	Phase 2
0.6822	Remote Similarity	NPD6084	Phase 2
0.6803	Remote Similarity	NPD6336	Discontinued
0.68	Remote Similarity	NPD4197	Approved
0.6796	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6101	Approved
0.678	Remote Similarity	NPD6314	Approved
0.678	Remote Similarity	NPD6313	Approved
0.6765	Remote Similarity	NPD3573	Approved
0.6762	Remote Similarity	NPD6399	Phase 3
0.6752	Remote Similarity	NPD6274	Approved
0.675	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8293	Discontinued
0.6733	Remote Similarity	NPD1694	Approved
0.6729	Remote Similarity	NPD7614	Phase 1
0.6727	Remote Similarity	NPD5091	Approved
0.6723	Remote Similarity	NPD4522	Approved
0.6699	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD5737	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6695	Remote Similarity	NPD7115	Discovery
0.6695	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6637	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5695	Phase 3
0.6606	Remote Similarity	NPD7638	Approved
0.66	Remote Similarity	NPD4221	Approved
0.66	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD1696	Phase 3
0.6545	Remote Similarity	NPD7639	Approved
0.6545	Remote Similarity	NPD7640	Approved
0.6535	Remote Similarity	NPD4788	Approved
0.6505	Remote Similarity	NPD7146	Approved
0.6505	Remote Similarity	NPD4623	Approved
0.6505	Remote Similarity	NPD6684	Approved
0.6505	Remote Similarity	NPD6409	Approved
0.6505	Remote Similarity	NPD4519	Discontinued
0.6505	Remote Similarity	NPD7334	Approved
0.6505	Remote Similarity	NPD7521	Approved
0.6505	Remote Similarity	NPD5330	Approved
0.6484	Remote Similarity	NPD7341	Phase 2
0.6475	Remote Similarity	NPD6921	Approved
0.6475	Remote Similarity	NPD6909	Approved
0.6475	Remote Similarity	NPD6908	Approved
0.6471	Remote Similarity	NPD3668	Phase 3
0.6455	Remote Similarity	NPD4225	Approved
0.6436	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7732	Phase 3
0.6415	Remote Similarity	NPD5785	Approved
0.6413	Remote Similarity	NPD7331	Phase 2
0.6408	Remote Similarity	NPD5363	Approved
0.64	Remote Similarity	NPD7525	Registered
0.6392	Remote Similarity	NPD3703	Phase 2
0.6381	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6903	Approved
0.6379	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6110	Phase 1
0.6364	Remote Similarity	NPD6334	Approved
0.6364	Remote Similarity	NPD6333	Approved
0.6357	Remote Similarity	NPD6845	Suspended
0.6346	Remote Similarity	NPD4690	Approved
0.6346	Remote Similarity	NPD4688	Approved
0.6346	Remote Similarity	NPD5205	Approved
0.6346	Remote Similarity	NPD4138	Approved
0.6346	Remote Similarity	NPD4693	Phase 3
0.6346	Remote Similarity	NPD4689	Approved
0.633	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6673	Approved
0.6321	Remote Similarity	NPD6904	Approved
0.6321	Remote Similarity	NPD6080	Approved
0.63	Remote Similarity	NPD7645	Phase 2
0.63	Remote Similarity	NPD4195	Approved
0.6296	Remote Similarity	NPD5133	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