NPASS Compound

Structure

CID310236 OpenBabel06191716122D 25 28 0 0 1 0 0 0 0 0999 V2000 7.6921 -1.7932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7262 -2.0520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0191 -1.3449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 -1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3461 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 -1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8771 0.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8862 3.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1249 1.6238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3611 2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0580 3.1533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 1.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3482 2.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3173 4.0802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7036 3.5138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9801 1.8040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 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 9 10 2 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 8 1 6 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 9 1 1 0 0 0 14 20 1 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 11 1 1 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 11 1 6 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 23 1 6 0 0 0 20 21 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.24
Volume:	373.304
LogP:	5.935
LogD:	4.356
LogS:	-4.168
# Rotatable Bonds:	8
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.195
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.876
MDCK Permeability:	3.3527201594552025e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.208
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	98.8033218383789%
Volume Distribution (VD):	1.383
Pgp-substrate:	1.7970247268676758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.217
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.347
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.683
CYP3A4-inhibitor:	0.244
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	4.302
Half-life (T1/2):	0.496

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.574
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.757
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC310236

Natural Product ID:	NPC310236
*Common Name:**	Beilschmiedic Acid A
IUPAC Name:	n.a.
Synonyms:	Beilschmiedic Acid A
Standard InCHIKey:	SBFRUSBMDXTFNO-KIBIGZOQSA-N
Standard InCHI:	InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-13-14-9-10-15-17(22(24)25)12-19(23)18-11-16(13)20(14)21(15)18/h9-10,12-16,18-21,23H,2-8,11H2,1H3,(H,24,25)/t13-,14-,15+,16+,18+,19+,20-,21+/m1/s1
SMILES:	CCCCCCCC[C@@H]1[C@H]2C=C[C@H]3C(=C[C@@H]([C@@H]4C[C@@H]1[C@@H]2[C@@H]34)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071413
PubChem CID:	42646683
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3622	Petrosia similis	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346970]
NPO32633	gabonese sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22758788]
NPO8683	Aristea ecklonii	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3622	Petrosia similis	Species	Petrosiidae	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
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	6100.0	nM	PMID[476610]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	10.0	ug.mL-1	PMID[476610]

☑ 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 NPC310236 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	173
0.1-0.2	970
0.2-0.3	5227
0.3-0.4	15036
0.4-0.5	9931
0.5-0.6	6898
0.6-0.7	3767
0.7-0.8	675
0.8-0.85	13
0.85-0.9	4
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC249889
0.988	High Similarity	NPC193843
0.8916	High Similarity	NPC271104
0.8864	High Similarity	NPC214387
0.8764	High Similarity	NPC477147
0.8764	High Similarity	NPC477149
0.8721	High Similarity	NPC165064
0.8696	High Similarity	NPC472941
0.8696	High Similarity	NPC456
0.8511	High Similarity	NPC166745
0.8511	High Similarity	NPC197386
0.8511	High Similarity	NPC235464
0.8506	High Similarity	NPC164577
0.8444	Intermediate Similarity	NPC123912
0.8421	Intermediate Similarity	NPC287833
0.8409	Intermediate Similarity	NPC474083
0.8391	Intermediate Similarity	NPC97913
0.8387	Intermediate Similarity	NPC469995
0.8387	Intermediate Similarity	NPC173875
0.8387	Intermediate Similarity	NPC476174
0.8387	Intermediate Similarity	NPC318282
0.8387	Intermediate Similarity	NPC174948
0.837	Intermediate Similarity	NPC474736
0.8333	Intermediate Similarity	NPC472924
0.8333	Intermediate Similarity	NPC224720
0.8333	Intermediate Similarity	NPC476240
0.8333	Intermediate Similarity	NPC476223
0.8298	Intermediate Similarity	NPC250757
0.8298	Intermediate Similarity	NPC301534
0.8298	Intermediate Similarity	NPC328371
0.8295	Intermediate Similarity	NPC473246
0.8295	Intermediate Similarity	NPC472865
0.828	Intermediate Similarity	NPC469406
0.8261	Intermediate Similarity	NPC204341
0.8261	Intermediate Similarity	NPC475806
0.8261	Intermediate Similarity	NPC212948
0.8247	Intermediate Similarity	NPC293753
0.8242	Intermediate Similarity	NPC309603
0.8242	Intermediate Similarity	NPC146554
0.8242	Intermediate Similarity	NPC473999
0.8242	Intermediate Similarity	NPC66344
0.8242	Intermediate Similarity	NPC262858
0.8242	Intermediate Similarity	NPC472240
0.8242	Intermediate Similarity	NPC155479
0.8242	Intermediate Similarity	NPC262043
0.8229	Intermediate Similarity	NPC241221
0.8229	Intermediate Similarity	NPC476274
0.8229	Intermediate Similarity	NPC51370
0.8222	Intermediate Similarity	NPC236618
0.8222	Intermediate Similarity	NPC287079
0.8222	Intermediate Similarity	NPC159046
0.8222	Intermediate Similarity	NPC233836
0.8222	Intermediate Similarity	NPC187376
0.8222	Intermediate Similarity	NPC312215
0.8211	Intermediate Similarity	NPC320306
0.8202	Intermediate Similarity	NPC471224
0.8202	Intermediate Similarity	NPC29447
0.8191	Intermediate Similarity	NPC259286
0.8172	Intermediate Similarity	NPC214697
0.8172	Intermediate Similarity	NPC472930
0.8172	Intermediate Similarity	NPC69454
0.8161	Intermediate Similarity	NPC477372
0.8152	Intermediate Similarity	NPC469400
0.8152	Intermediate Similarity	NPC46281
0.8152	Intermediate Similarity	NPC48010
0.8144	Intermediate Similarity	NPC99411
0.8132	Intermediate Similarity	NPC117122
0.8132	Intermediate Similarity	NPC294480
0.8132	Intermediate Similarity	NPC472870
0.8125	Intermediate Similarity	NPC471717
0.8111	Intermediate Similarity	NPC28252
0.8111	Intermediate Similarity	NPC222613
0.8111	Intermediate Similarity	NPC212843
0.8111	Intermediate Similarity	NPC118648
0.8111	Intermediate Similarity	NPC155011
0.8111	Intermediate Similarity	NPC55309
0.8111	Intermediate Similarity	NPC472869
0.8111	Intermediate Similarity	NPC186975
0.8111	Intermediate Similarity	NPC475022
0.8111	Intermediate Similarity	NPC194417
0.8105	Intermediate Similarity	NPC249954
0.8105	Intermediate Similarity	NPC29152
0.81	Intermediate Similarity	NPC91034
0.809	Intermediate Similarity	NPC472864
0.809	Intermediate Similarity	NPC194937
0.809	Intermediate Similarity	NPC85774
0.809	Intermediate Similarity	NPC476038
0.809	Intermediate Similarity	NPC214043
0.809	Intermediate Similarity	NPC19849
0.8085	Intermediate Similarity	NPC8993
0.8085	Intermediate Similarity	NPC184870
0.8068	Intermediate Similarity	NPC142253
0.8068	Intermediate Similarity	NPC3511
0.8065	Intermediate Similarity	NPC473986
0.8065	Intermediate Similarity	NPC45269
0.8065	Intermediate Similarity	NPC476187
0.8065	Intermediate Similarity	NPC63748
0.8065	Intermediate Similarity	NPC233116
0.8065	Intermediate Similarity	NPC474018
0.8065	Intermediate Similarity	NPC473998
0.8065	Intermediate Similarity	NPC470113
0.8061	Intermediate Similarity	NPC204450
0.8061	Intermediate Similarity	NPC234892
0.8061	Intermediate Similarity	NPC195290
0.8043	Intermediate Similarity	NPC84271
0.8043	Intermediate Similarity	NPC77168
0.8043	Intermediate Similarity	NPC102414
0.8043	Intermediate Similarity	NPC2983
0.8041	Intermediate Similarity	NPC327431
0.8023	Intermediate Similarity	NPC192006
0.8022	Intermediate Similarity	NPC128644
0.8022	Intermediate Similarity	NPC136548
0.8022	Intermediate Similarity	NPC312561
0.8022	Intermediate Similarity	NPC136948
0.8022	Intermediate Similarity	NPC142361
0.8022	Intermediate Similarity	NPC58063
0.8022	Intermediate Similarity	NPC93778
0.8022	Intermediate Similarity	NPC474684
0.8021	Intermediate Similarity	NPC253826
0.8021	Intermediate Similarity	NPC107243
0.8021	Intermediate Similarity	NPC156546
0.8021	Intermediate Similarity	NPC108078
0.8021	Intermediate Similarity	NPC202705
0.8	Intermediate Similarity	NPC37646
0.8	Intermediate Similarity	NPC279537
0.8	Intermediate Similarity	NPC472932
0.8	Intermediate Similarity	NPC269638
0.8	Intermediate Similarity	NPC293052
0.8	Intermediate Similarity	NPC283733
0.798	Intermediate Similarity	NPC236390
0.7979	Intermediate Similarity	NPC115021
0.7979	Intermediate Similarity	NPC243866
0.7978	Intermediate Similarity	NPC310470
0.7978	Intermediate Similarity	NPC49019
0.7976	Intermediate Similarity	NPC55527
0.7959	Intermediate Similarity	NPC282524
0.7959	Intermediate Similarity	NPC146822
0.7959	Intermediate Similarity	NPC302537
0.7959	Intermediate Similarity	NPC163372
0.7957	Intermediate Similarity	NPC191684
0.7957	Intermediate Similarity	NPC69622
0.7955	Intermediate Similarity	NPC201912
0.7955	Intermediate Similarity	NPC38350
0.7938	Intermediate Similarity	NPC98868
0.7938	Intermediate Similarity	NPC108368
0.7938	Intermediate Similarity	NPC57079
0.7938	Intermediate Similarity	NPC48647
0.7938	Intermediate Similarity	NPC103051
0.7935	Intermediate Similarity	NPC183546
0.7935	Intermediate Similarity	NPC48866
0.7935	Intermediate Similarity	NPC471722
0.7935	Intermediate Similarity	NPC104560
0.7935	Intermediate Similarity	NPC242864
0.7935	Intermediate Similarity	NPC247406
0.7931	Intermediate Similarity	NPC477371
0.7921	Intermediate Similarity	NPC472925
0.7917	Intermediate Similarity	NPC3772
0.7917	Intermediate Similarity	NPC155676
0.7917	Intermediate Similarity	NPC40765
0.7917	Intermediate Similarity	NPC243525
0.7917	Intermediate Similarity	NPC7124
0.7912	Intermediate Similarity	NPC82979
0.7912	Intermediate Similarity	NPC31564
0.7912	Intermediate Similarity	NPC474733
0.7912	Intermediate Similarity	NPC72133
0.7912	Intermediate Similarity	NPC474778
0.7912	Intermediate Similarity	NPC469994
0.7912	Intermediate Similarity	NPC145879
0.7912	Intermediate Similarity	NPC474732
0.7895	Intermediate Similarity	NPC299100
0.7895	Intermediate Similarity	NPC166906
0.7895	Intermediate Similarity	NPC7165
0.7889	Intermediate Similarity	NPC87552
0.7879	Intermediate Similarity	NPC308726
0.7879	Intermediate Similarity	NPC119601
0.7879	Intermediate Similarity	NPC475320
0.7872	Intermediate Similarity	NPC110923
0.7872	Intermediate Similarity	NPC272746
0.7872	Intermediate Similarity	NPC107690
0.7872	Intermediate Similarity	NPC74296
0.7865	Intermediate Similarity	NPC472239
0.7865	Intermediate Similarity	NPC320514
0.7865	Intermediate Similarity	NPC260956
0.7865	Intermediate Similarity	NPC224455
0.7864	Intermediate Similarity	NPC37116
0.7857	Intermediate Similarity	NPC266955
0.7857	Intermediate Similarity	NPC35656
0.7857	Intermediate Similarity	NPC201406
0.7857	Intermediate Similarity	NPC470074
0.7849	Intermediate Similarity	NPC477215
0.7849	Intermediate Similarity	NPC476388
0.7849	Intermediate Similarity	NPC128496
0.7849	Intermediate Similarity	NPC86319
0.7849	Intermediate Similarity	NPC474704
0.7849	Intermediate Similarity	NPC5509
0.7849	Intermediate Similarity	NPC475921
0.7849	Intermediate Similarity	NPC275740
0.7849	Intermediate Similarity	NPC54689
0.7843	Intermediate Similarity	NPC220155
0.7843	Intermediate Similarity	NPC295244

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 NPC310236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1495
0.2-0.3	3928
0.3-0.4	2471
0.4-0.5	648
0.5-0.6	244
0.6-0.7	185
0.7-0.8	25
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
0.7872	Intermediate Similarity	NPD6079	Approved
0.7816	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD5363	Approved
0.7778	Intermediate Similarity	NPD5362	Discontinued
0.7717	Intermediate Similarity	NPD5279	Phase 3
0.7692	Intermediate Similarity	NPD3666	Approved
0.7692	Intermediate Similarity	NPD3665	Phase 1
0.7692	Intermediate Similarity	NPD3133	Approved
0.7692	Intermediate Similarity	NPD4786	Approved
0.766	Intermediate Similarity	NPD5328	Approved
0.7527	Intermediate Similarity	NPD6684	Approved
0.7527	Intermediate Similarity	NPD5690	Phase 2
0.7527	Intermediate Similarity	NPD7334	Approved
0.7527	Intermediate Similarity	NPD5330	Approved
0.7527	Intermediate Similarity	NPD3618	Phase 1
0.7527	Intermediate Similarity	NPD6409	Approved
0.7527	Intermediate Similarity	NPD7146	Approved
0.7527	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD6404	Discontinued
0.75	Intermediate Similarity	NPD5284	Approved
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7473	Intermediate Similarity	NPD4269	Approved
0.7473	Intermediate Similarity	NPD3667	Approved
0.7473	Intermediate Similarity	NPD4270	Approved
0.7449	Intermediate Similarity	NPD5695	Phase 3
0.7423	Intermediate Similarity	NPD5778	Approved
0.7423	Intermediate Similarity	NPD6399	Phase 3
0.7423	Intermediate Similarity	NPD5779	Approved
0.7396	Intermediate Similarity	NPD5785	Approved
0.7391	Intermediate Similarity	NPD5332	Approved
0.7391	Intermediate Similarity	NPD5331	Approved
0.7374	Intermediate Similarity	NPD5221	Approved
0.7374	Intermediate Similarity	NPD5222	Approved
0.7374	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6903	Approved
0.7368	Intermediate Similarity	NPD6672	Approved
0.7368	Intermediate Similarity	NPD5737	Approved
0.7368	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4790	Discontinued
0.7353	Intermediate Similarity	NPD5211	Phase 2
0.7333	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6899	Approved
0.7327	Intermediate Similarity	NPD7639	Approved
0.7327	Intermediate Similarity	NPD7640	Approved
0.732	Intermediate Similarity	NPD7515	Phase 2
0.73	Intermediate Similarity	NPD5173	Approved
0.7292	Intermediate Similarity	NPD4753	Phase 2
0.7283	Intermediate Similarity	NPD4221	Approved
0.7283	Intermediate Similarity	NPD4223	Phase 3
0.7273	Intermediate Similarity	NPD5210	Approved
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD4629	Approved
0.7253	Intermediate Similarity	NPD4820	Approved
0.7253	Intermediate Similarity	NPD4821	Approved
0.7253	Intermediate Similarity	NPD4252	Approved
0.7253	Intermediate Similarity	NPD4822	Approved
0.7253	Intermediate Similarity	NPD4819	Approved
0.7245	Intermediate Similarity	NPD4202	Approved
0.7238	Intermediate Similarity	NPD5697	Approved
0.7234	Intermediate Similarity	NPD5329	Approved
0.7234	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7638	Approved
0.7222	Intermediate Similarity	NPD4271	Approved
0.7222	Intermediate Similarity	NPD4268	Approved
0.7212	Intermediate Similarity	NPD5141	Approved
0.7204	Intermediate Similarity	NPD7154	Phase 3
0.7196	Intermediate Similarity	NPD7290	Approved
0.7196	Intermediate Similarity	NPD7102	Approved
0.7196	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD6011	Approved
0.7158	Intermediate Similarity	NPD4694	Approved
0.7158	Intermediate Similarity	NPD4623	Approved
0.7158	Intermediate Similarity	NPD4519	Discontinued
0.7158	Intermediate Similarity	NPD5280	Approved
0.7158	Intermediate Similarity	NPD5786	Approved
0.7157	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD5286	Approved
0.7157	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD8130	Phase 1
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6847	Approved
0.7128	Intermediate Similarity	NPD4197	Approved
0.7113	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6101	Approved
0.7103	Intermediate Similarity	NPD6013	Approved
0.7103	Intermediate Similarity	NPD6014	Approved
0.7103	Intermediate Similarity	NPD6012	Approved
0.7097	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5223	Approved
0.7065	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5368	Approved
0.7064	Intermediate Similarity	NPD6053	Discontinued
0.7064	Intermediate Similarity	NPD6882	Approved
0.7064	Intermediate Similarity	NPD8297	Approved
0.7059	Intermediate Similarity	NPD5696	Approved
0.7053	Intermediate Similarity	NPD1694	Approved
0.7041	Intermediate Similarity	NPD5207	Approved
0.703	Intermediate Similarity	NPD4697	Phase 3
0.7021	Intermediate Similarity	NPD4788	Approved
0.7019	Intermediate Similarity	NPD5225	Approved
0.7019	Intermediate Similarity	NPD5226	Approved
0.7019	Intermediate Similarity	NPD4633	Approved
0.7019	Intermediate Similarity	NPD5224	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6989	Remote Similarity	NPD5369	Approved
0.6979	Remote Similarity	NPD5205	Approved
0.6979	Remote Similarity	NPD4690	Approved
0.6979	Remote Similarity	NPD4689	Approved
0.6979	Remote Similarity	NPD4688	Approved
0.6979	Remote Similarity	NPD4138	Approved
0.6979	Remote Similarity	NPD4693	Phase 3
0.697	Remote Similarity	NPD6411	Approved
0.697	Remote Similarity	NPD7637	Suspended
0.697	Remote Similarity	NPD5694	Approved
0.697	Remote Similarity	NPD6050	Approved
0.6961	Remote Similarity	NPD4755	Approved
0.6957	Remote Similarity	NPD4195	Approved
0.6952	Remote Similarity	NPD5174	Approved
0.6952	Remote Similarity	NPD5175	Approved
0.6944	Remote Similarity	NPD6373	Approved
0.6944	Remote Similarity	NPD6372	Approved
0.6939	Remote Similarity	NPD6673	Approved
0.6939	Remote Similarity	NPD6904	Approved
0.6939	Remote Similarity	NPD6080	Approved
0.6916	Remote Similarity	NPD5701	Approved
0.6915	Remote Similarity	NPD6435	Approved
0.6889	Remote Similarity	NPD6942	Approved
0.6889	Remote Similarity	NPD7339	Approved
0.6875	Remote Similarity	NPD6868	Approved
0.6869	Remote Similarity	NPD5692	Phase 3
0.6848	Remote Similarity	NPD3617	Approved
0.6847	Remote Similarity	NPD4632	Approved
0.6837	Remote Similarity	NPD4518	Approved
0.6837	Remote Similarity	NPD5208	Approved
0.6827	Remote Similarity	NPD4700	Approved
0.6818	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6098	Approved
0.68	Remote Similarity	NPD5693	Phase 1
0.6796	Remote Similarity	NPD7902	Approved
0.6778	Remote Similarity	NPD4687	Approved
0.6778	Remote Similarity	NPD5733	Approved
0.6771	Remote Similarity	NPD3668	Phase 3
0.6768	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6335	Approved
0.6731	Remote Similarity	NPD4225	Approved
0.6703	Remote Similarity	NPD8264	Approved
0.6702	Remote Similarity	NPD4695	Discontinued
0.6701	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4096	Approved
0.6698	Remote Similarity	NPD7632	Discontinued
0.6697	Remote Similarity	NPD5168	Approved
0.6697	Remote Similarity	NPD4730	Approved
0.6697	Remote Similarity	NPD6686	Approved
0.6697	Remote Similarity	NPD4729	Approved
0.6696	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6636	Remote Similarity	NPD4754	Approved
0.6634	Remote Similarity	NPD8035	Phase 2
0.6634	Remote Similarity	NPD8034	Phase 2
0.6632	Remote Similarity	NPD4139	Approved
0.6632	Remote Similarity	NPD4692	Approved
0.663	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4691	Approved
0.6629	Remote Similarity	NPD4747	Approved
0.6609	Remote Similarity	NPD6313	Approved
0.6609	Remote Similarity	NPD6314	Approved
0.6606	Remote Similarity	NPD6412	Phase 2
0.66	Remote Similarity	NPD6051	Approved
0.6596	Remote Similarity	NPD6929	Approved
0.6593	Remote Similarity	NPD6926	Approved
0.6593	Remote Similarity	NPD6924	Approved
0.6593	Remote Similarity	NPD4058	Approved
0.6593	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6274	Approved
0.6577	Remote Similarity	NPD4634	Approved
0.6577	Remote Similarity	NPD5250	Approved
0.6577	Remote Similarity	NPD5248	Approved
0.6577	Remote Similarity	NPD5169	Approved
0.6577	Remote Similarity	NPD5247	Approved
0.6577	Remote Similarity	NPD5251	Approved
0.6577	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5249	Phase 3
0.6577	Remote Similarity	NPD5135	Approved
0.6569	Remote Similarity	NPD5133	Approved
0.6566	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4250	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