NPASS Compound

Structure

CID2946 OpenBabel06191715322D 29 31 0 0 1 0 0 0 0 0999 V2000 0.0885 4.5817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6057 4.9418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9489 -1.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2735 -3.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 2.6254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0705 3.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6582 0.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6582 0.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6582 -2.0161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0998 -2.7507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2891 0.0737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8626 4.2727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3653 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6582 -2.0161 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2563 -1.7630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3653 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1122 -2.9071 0.0000 C 0 0 1 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 5.0825 -0.5351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1473 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1645 -3.9058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 26 2 0 0 0 0 17 3 1 6 0 0 0 17 25 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 1 0 0 0 20 22 1 0 0 0 0 20 27 2 0 0 0 0 21 23 1 6 0 0 0 21 25 1 0 0 0 0 22 18 1 1 0 0 0 23 4 1 6 0 0 0 24 5 1 6 0 0 0 24 28 1 0 0 0 0 25 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.28
Volume:	439.902
LogP:	4.688
LogD:	3.634
LogS:	-4.849
# Rotatable Bonds:	5
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	5.074
Fsp3:	0.76
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:	-4.677
MDCK Permeability:	2.475537985446863e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.122
20% Bioavailability (F20%):	0.861
30% Bioavailability (F30%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	94.07317352294922%
Volume Distribution (VD):	1.609
Pgp-substrate:	4.095820903778076%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.355
CYP2C19-substrate:	0.661
CYP2C9-inhibitor:	0.236
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.235
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.375

ADMET: Excretion

Clearance (CL):	6.85
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.295
Human Hepatotoxicity (H-HT):	0.515
Drug-inuced Liver Injury (DILI):	0.109
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.949
Carcinogencity:	0.684
Eye Corrosion:	0.054
Eye Irritation:	0.151
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC2946

Natural Product ID:	NPC2946
*Common Name:**	Ophiobolin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SXRLPRKYTRWOES-PCQMDVLKSA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-16(2)7-6-8-17(3)25(29)12-11-23(4)13-19-22(20(27)14-24(19,5)28)18(15-26)9-10-21(23)25/h7,9,15,17,19,21-22,28-29H,6,8,10-14H2,1-5H3/b18-9-/t17-,19-,21+,22+,23+,24+,25-/m0/s1
SMILES:	CC(=CCC[C@H](C)[C@]1(CC[C@]2(C)C[C@H]3[C@@H](C(=CC[C@@H]12)C=O)C(=O)C[C@@]3(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478388
PubChem CID:	12303081
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
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395513]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO13275	Centaurea scabiosa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO2613	Artemisia ordosica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5756	Amanita abrupta	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16542	Aloe rupestris	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5119.2	Pseudomonas chlororaphis subsp. aureofaciens	Subspecies	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15571	Iphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11651	Parsonsia heterophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16867	Bursera permollis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13275	Centaurea scabiosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2990	Solenostemon scutellarioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12794	Hypericum pseudopetiolatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IZ	<=	1.0	mm	PMID[571138]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	7.0	mm	PMID[571138]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	3.0	mm	PMID[571138]

☑ 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 NPC2946 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	210
0.1-0.2	1693
0.2-0.3	8576
0.3-0.4	15160
0.4-0.5	8649
0.5-0.6	6235
0.6-0.7	1983
0.7-0.8	167
0.8-0.85	12
0.85-0.9	7
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC41217
0.9032	High Similarity	NPC304738
0.9032	High Similarity	NPC195192
0.8667	High Similarity	NPC477711
0.8652	High Similarity	NPC477710
0.8214	Intermediate Similarity	NPC251435
0.8163	Intermediate Similarity	NPC25639
0.7978	Intermediate Similarity	NPC256750
0.7978	Intermediate Similarity	NPC20262
0.7955	Intermediate Similarity	NPC164218
0.7907	Intermediate Similarity	NPC215481
0.7872	Intermediate Similarity	NPC49946
0.7872	Intermediate Similarity	NPC306168
0.7841	Intermediate Similarity	NPC261125
0.7841	Intermediate Similarity	NPC181195
0.7841	Intermediate Similarity	NPC301769
0.7816	Intermediate Similarity	NPC276769
0.7812	Intermediate Similarity	NPC298919
0.7791	Intermediate Similarity	NPC77501
0.7766	Intermediate Similarity	NPC170775
0.7708	Intermediate Similarity	NPC125180
0.7708	Intermediate Similarity	NPC37816
0.7708	Intermediate Similarity	NPC474807
0.77	Intermediate Similarity	NPC237190
0.7692	Intermediate Similarity	NPC474748
0.7692	Intermediate Similarity	NPC62214
0.764	Intermediate Similarity	NPC32758
0.7609	Intermediate Similarity	NPC475796
0.7582	Intermediate Similarity	NPC477271
0.7582	Intermediate Similarity	NPC477269
0.7582	Intermediate Similarity	NPC129080
0.7582	Intermediate Similarity	NPC477270
0.7579	Intermediate Similarity	NPC477943
0.7579	Intermediate Similarity	NPC123912
0.7558	Intermediate Similarity	NPC300940
0.7528	Intermediate Similarity	NPC228911
0.7525	Intermediate Similarity	NPC477950
0.7525	Intermediate Similarity	NPC475099
0.7524	Intermediate Similarity	NPC475941
0.7524	Intermediate Similarity	NPC474901
0.75	Intermediate Similarity	NPC469646
0.75	Intermediate Similarity	NPC147954
0.75	Intermediate Similarity	NPC477355
0.7476	Intermediate Similarity	NPC13385
0.7474	Intermediate Similarity	NPC472677
0.7474	Intermediate Similarity	NPC472483
0.7474	Intermediate Similarity	NPC58532
0.7449	Intermediate Similarity	NPC90453
0.7442	Intermediate Similarity	NPC469737
0.7426	Intermediate Similarity	NPC474720
0.74	Intermediate Similarity	NPC477268
0.74	Intermediate Similarity	NPC477267
0.74	Intermediate Similarity	NPC472689
0.74	Intermediate Similarity	NPC472690
0.74	Intermediate Similarity	NPC87090
0.7396	Intermediate Similarity	NPC232747
0.7396	Intermediate Similarity	NPC477215
0.7396	Intermediate Similarity	NPC476388
0.7391	Intermediate Similarity	NPC133844
0.7386	Intermediate Similarity	NPC201263
0.7379	Intermediate Similarity	NPC474207
0.7379	Intermediate Similarity	NPC470839
0.7379	Intermediate Similarity	NPC474330
0.7363	Intermediate Similarity	NPC45495
0.7363	Intermediate Similarity	NPC279667
0.7363	Intermediate Similarity	NPC471656
0.7353	Intermediate Similarity	NPC477356
0.7353	Intermediate Similarity	NPC270155
0.7353	Intermediate Similarity	NPC475867
0.7347	Intermediate Similarity	NPC250575
0.7333	Intermediate Similarity	NPC220974
0.7333	Intermediate Similarity	NPC43285
0.7333	Intermediate Similarity	NPC58370
0.732	Intermediate Similarity	NPC472476
0.732	Intermediate Similarity	NPC171441
0.7315	Intermediate Similarity	NPC475970
0.7303	Intermediate Similarity	NPC141346
0.7303	Intermediate Similarity	NPC124289
0.7303	Intermediate Similarity	NPC226242
0.7303	Intermediate Similarity	NPC473437
0.7303	Intermediate Similarity	NPC25908
0.7303	Intermediate Similarity	NPC142759
0.7303	Intermediate Similarity	NPC115719
0.73	Intermediate Similarity	NPC121036
0.73	Intermediate Similarity	NPC472674
0.73	Intermediate Similarity	NPC192428
0.7292	Intermediate Similarity	NPC471941
0.7283	Intermediate Similarity	NPC171665
0.7282	Intermediate Similarity	NPC118405
0.7282	Intermediate Similarity	NPC87351
0.7253	Intermediate Similarity	NPC7232
0.7253	Intermediate Similarity	NPC164308
0.7234	Intermediate Similarity	NPC7927
0.7234	Intermediate Similarity	NPC230527
0.7228	Intermediate Similarity	NPC477949
0.7216	Intermediate Similarity	NPC326627
0.7216	Intermediate Similarity	NPC310010
0.7216	Intermediate Similarity	NPC97032
0.7212	Intermediate Similarity	NPC311612
0.7212	Intermediate Similarity	NPC111323
0.7209	Intermediate Similarity	NPC469914
0.7204	Intermediate Similarity	NPC193347
0.72	Intermediate Similarity	NPC472932
0.7196	Intermediate Similarity	NPC470257
0.7191	Intermediate Similarity	NPC472256
0.7191	Intermediate Similarity	NPC474011
0.7188	Intermediate Similarity	NPC472482
0.7188	Intermediate Similarity	NPC472493
0.7188	Intermediate Similarity	NPC472481
0.7188	Intermediate Similarity	NPC472484
0.7184	Intermediate Similarity	NPC206079
0.7174	Intermediate Similarity	NPC30675
0.7172	Intermediate Similarity	NPC233118
0.7172	Intermediate Similarity	NPC477361
0.7172	Intermediate Similarity	NPC25750
0.7172	Intermediate Similarity	NPC202824
0.7158	Intermediate Similarity	NPC36350
0.7158	Intermediate Similarity	NPC474218
0.7158	Intermediate Similarity	NPC469948
0.7158	Intermediate Similarity	NPC476628
0.7157	Intermediate Similarity	NPC197386
0.7157	Intermediate Similarity	NPC109556
0.7143	Intermediate Similarity	NPC191684
0.7143	Intermediate Similarity	NPC183283
0.7129	Intermediate Similarity	NPC49371
0.7129	Intermediate Similarity	NPC477354
0.7129	Intermediate Similarity	NPC471463
0.7128	Intermediate Similarity	NPC65350
0.7128	Intermediate Similarity	NPC278648
0.7128	Intermediate Similarity	NPC476082
0.7128	Intermediate Similarity	NPC470165
0.7128	Intermediate Similarity	NPC477373
0.7115	Intermediate Similarity	NPC195290
0.7115	Intermediate Similarity	NPC204450
0.7115	Intermediate Similarity	NPC473424
0.7115	Intermediate Similarity	NPC477915
0.7113	Intermediate Similarity	NPC474854
0.7113	Intermediate Similarity	NPC328313
0.7113	Intermediate Similarity	NPC476708
0.7103	Intermediate Similarity	NPC177064
0.7103	Intermediate Similarity	NPC469508
0.7097	Intermediate Similarity	NPC47031
0.7097	Intermediate Similarity	NPC90055
0.7087	Intermediate Similarity	NPC144956
0.7087	Intermediate Similarity	NPC280963
0.7083	Intermediate Similarity	NPC232156
0.7083	Intermediate Similarity	NPC183736
0.7079	Intermediate Similarity	NPC469691
0.7079	Intermediate Similarity	NPC167049
0.7079	Intermediate Similarity	NPC206875
0.7071	Intermediate Similarity	NPC221282
0.7071	Intermediate Similarity	NPC290651
0.7065	Intermediate Similarity	NPC471890
0.7065	Intermediate Similarity	NPC66677
0.7065	Intermediate Similarity	NPC84185
0.7059	Intermediate Similarity	NPC18509
0.7059	Intermediate Similarity	NPC213947
0.7059	Intermediate Similarity	NPC108475
0.7059	Intermediate Similarity	NPC170143
0.7053	Intermediate Similarity	NPC470812
0.7053	Intermediate Similarity	NPC472480
0.7053	Intermediate Similarity	NPC144258
0.7053	Intermediate Similarity	NPC82902
0.7053	Intermediate Similarity	NPC329043
0.7053	Intermediate Similarity	NPC161423
0.7053	Intermediate Similarity	NPC321187
0.7053	Intermediate Similarity	NPC214043
0.7053	Intermediate Similarity	NPC58841
0.7053	Intermediate Similarity	NPC227064
0.7053	Intermediate Similarity	NPC473246
0.7053	Intermediate Similarity	NPC85774
0.7048	Intermediate Similarity	NPC117185
0.7048	Intermediate Similarity	NPC36321
0.7048	Intermediate Similarity	NPC236390
0.7041	Intermediate Similarity	NPC117405
0.7041	Intermediate Similarity	NPC86319
0.7041	Intermediate Similarity	NPC52198
0.7041	Intermediate Similarity	NPC472477
0.7041	Intermediate Similarity	NPC275740
0.7041	Intermediate Similarity	NPC184663
0.7041	Intermediate Similarity	NPC472475
0.7041	Intermediate Similarity	NPC116146
0.7041	Intermediate Similarity	NPC24772
0.703	Intermediate Similarity	NPC476487
0.703	Intermediate Similarity	NPC279313
0.703	Intermediate Similarity	NPC241156
0.703	Intermediate Similarity	NPC263347
0.703	Intermediate Similarity	NPC476488
0.703	Intermediate Similarity	NPC472469
0.7021	Intermediate Similarity	NPC7414
0.7021	Intermediate Similarity	NPC133391
0.7019	Intermediate Similarity	NPC171759
0.7019	Intermediate Similarity	NPC472924
0.701	Intermediate Similarity	NPC93778
0.701	Intermediate Similarity	NPC96496
0.701	Intermediate Similarity	NPC312215
0.701	Intermediate Similarity	NPC317590
0.7009	Intermediate Similarity	NPC185
0.7	Intermediate Similarity	NPC469678
0.7	Intermediate Similarity	NPC475771

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 NPC2946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	2490
0.2-0.3	4228
0.3-0.4	1586
0.4-0.5	321
0.5-0.6	163
0.6-0.7	162
0.7-0.8	4
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
0.734	Intermediate Similarity	NPD5363	Approved
0.732	Intermediate Similarity	NPD5785	Approved
0.73	Intermediate Similarity	NPD4697	Phase 3
0.7283	Intermediate Similarity	NPD5369	Approved
0.7263	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5786	Approved
0.7216	Intermediate Similarity	NPD4753	Phase 2
0.7204	Intermediate Similarity	NPD4221	Approved
0.7204	Intermediate Similarity	NPD4223	Phase 3
0.72	Intermediate Similarity	NPD4629	Approved
0.72	Intermediate Similarity	NPD5210	Approved
0.7158	Intermediate Similarity	NPD5329	Approved
0.7087	Intermediate Similarity	NPD5286	Approved
0.7087	Intermediate Similarity	NPD5285	Approved
0.7087	Intermediate Similarity	NPD4696	Approved
0.7083	Intermediate Similarity	NPD5690	Phase 2
0.7071	Intermediate Similarity	NPD6079	Approved
0.7059	Intermediate Similarity	NPD4755	Approved
0.7053	Intermediate Similarity	NPD4197	Approved
0.7053	Intermediate Similarity	NPD3665	Phase 1
0.7053	Intermediate Similarity	NPD3133	Approved
0.7053	Intermediate Similarity	NPD3666	Approved
0.7041	Intermediate Similarity	NPD5328	Approved
0.7021	Intermediate Similarity	NPD4269	Approved
0.7021	Intermediate Similarity	NPD4270	Approved
0.7021	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5223	Approved
0.6989	Remote Similarity	NPD5368	Approved
0.6952	Remote Similarity	NPD5211	Phase 2
0.6952	Remote Similarity	NPD5225	Approved
0.6952	Remote Similarity	NPD5226	Approved
0.6952	Remote Similarity	NPD4633	Approved
0.6952	Remote Similarity	NPD5224	Approved
0.6947	Remote Similarity	NPD4788	Approved
0.6944	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD4700	Approved
0.6909	Remote Similarity	NPD6650	Approved
0.6909	Remote Similarity	NPD6649	Approved
0.6907	Remote Similarity	NPD5205	Approved
0.6907	Remote Similarity	NPD4689	Approved
0.6907	Remote Similarity	NPD4693	Phase 3
0.6907	Remote Similarity	NPD4138	Approved
0.6907	Remote Similarity	NPD4688	Approved
0.6907	Remote Similarity	NPD4694	Approved
0.6907	Remote Similarity	NPD4690	Approved
0.6907	Remote Similarity	NPD5280	Approved
0.69	Remote Similarity	NPD5281	Approved
0.69	Remote Similarity	NPD5284	Approved
0.6893	Remote Similarity	NPD6084	Phase 2
0.6893	Remote Similarity	NPD6083	Phase 2
0.6887	Remote Similarity	NPD5174	Approved
0.6887	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD6373	Approved
0.6881	Remote Similarity	NPD6372	Approved
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5695	Phase 3
0.686	Remote Similarity	NPD7331	Phase 2
0.6842	Remote Similarity	NPD6435	Approved
0.6832	Remote Similarity	NPD4202	Approved
0.6827	Remote Similarity	NPD5696	Approved
0.6822	Remote Similarity	NPD5141	Approved
0.6818	Remote Similarity	NPD4634	Approved
0.6809	Remote Similarity	NPD4252	Approved
0.6796	Remote Similarity	NPD5222	Approved
0.6796	Remote Similarity	NPD5221	Approved
0.6796	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6899	Approved
0.6789	Remote Similarity	NPD6881	Approved
0.6774	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5362	Discontinued
0.6768	Remote Similarity	NPD4518	Approved
0.6768	Remote Similarity	NPD6903	Approved
0.6765	Remote Similarity	NPD5282	Discontinued
0.6759	Remote Similarity	NPD7128	Approved
0.6759	Remote Similarity	NPD6402	Approved
0.6759	Remote Similarity	NPD6675	Approved
0.6759	Remote Similarity	NPD5739	Approved
0.6744	Remote Similarity	NPD7341	Phase 2
0.6735	Remote Similarity	NPD3618	Phase 1
0.6735	Remote Similarity	NPD5279	Phase 3
0.6731	Remote Similarity	NPD5173	Approved
0.6729	Remote Similarity	NPD4754	Approved
0.6702	Remote Similarity	NPD4195	Approved
0.6701	Remote Similarity	NPD4786	Approved
0.6699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6634	Remote Similarity	NPD4096	Approved
0.6607	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD8130	Phase 1
0.6607	Remote Similarity	NPD6617	Approved
0.6606	Remote Similarity	NPD4768	Approved
0.6606	Remote Similarity	NPD4767	Approved
0.6598	Remote Similarity	NPD5332	Approved
0.6598	Remote Similarity	NPD5331	Approved
0.6581	Remote Similarity	NPD6054	Approved
0.6577	Remote Similarity	NPD6013	Approved
0.6577	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6566	Remote Similarity	NPD6409	Approved
0.6566	Remote Similarity	NPD7334	Approved
0.6566	Remote Similarity	NPD6684	Approved
0.6566	Remote Similarity	NPD7146	Approved
0.6566	Remote Similarity	NPD5330	Approved
0.6566	Remote Similarity	NPD7521	Approved
0.6562	Remote Similarity	NPD4790	Discontinued
0.6549	Remote Similarity	NPD6882	Approved
0.6549	Remote Similarity	NPD8297	Approved
0.6545	Remote Similarity	NPD5701	Approved
0.6535	Remote Similarity	NPD6904	Approved
0.6535	Remote Similarity	NPD6673	Approved
0.6535	Remote Similarity	NPD6080	Approved
0.6518	Remote Similarity	NPD5135	Approved
0.6518	Remote Similarity	NPD5248	Approved
0.6518	Remote Similarity	NPD5251	Approved
0.6518	Remote Similarity	NPD5247	Approved
0.6518	Remote Similarity	NPD5250	Approved
0.6518	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6371	Approved
0.6518	Remote Similarity	NPD5249	Phase 3
0.6518	Remote Similarity	NPD5169	Approved
0.6495	Remote Similarity	NPD3667	Approved
0.6481	Remote Similarity	NPD5091	Approved
0.6471	Remote Similarity	NPD6370	Approved
0.6471	Remote Similarity	NPD5207	Approved
0.6465	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5127	Approved
0.646	Remote Similarity	NPD5215	Approved
0.646	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5216	Approved
0.646	Remote Similarity	NPD5217	Approved
0.6458	Remote Similarity	NPD4695	Discontinued
0.6455	Remote Similarity	NPD6008	Approved
0.6441	Remote Similarity	NPD6059	Approved
0.6436	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD6672	Approved
0.6436	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6050	Approved
0.6396	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7078	Approved
0.6392	Remote Similarity	NPD4139	Approved
0.6392	Remote Similarity	NPD4692	Approved
0.6387	Remote Similarity	NPD6016	Approved
0.6387	Remote Similarity	NPD6015	Approved
0.6364	Remote Similarity	NPD7492	Approved
0.6348	Remote Similarity	NPD4632	Approved
0.6346	Remote Similarity	NPD5133	Approved
0.6333	Remote Similarity	NPD5988	Approved
0.6311	Remote Similarity	NPD5692	Phase 3
0.6311	Remote Similarity	NPD6616	Approved
0.6303	Remote Similarity	NPD6319	Approved
0.6293	Remote Similarity	NPD5167	Approved
0.6289	Remote Similarity	NPD4819	Approved
0.6289	Remote Similarity	NPD4821	Approved
0.6289	Remote Similarity	NPD4822	Approved
0.6289	Remote Similarity	NPD4820	Approved
0.6286	Remote Similarity	NPD6001	Approved
0.6275	Remote Similarity	NPD5208	Approved
0.6271	Remote Similarity	NPD6335	Approved
0.6261	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3617	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD5694	Approved
0.6239	Remote Similarity	NPD6274	Approved
0.6238	Remote Similarity	NPD6098	Approved
0.6218	Remote Similarity	NPD7101	Approved
0.6218	Remote Similarity	NPD7100	Approved
0.621	Remote Similarity	NPD7736	Approved
0.62	Remote Similarity	NPD3668	Phase 3
0.6195	Remote Similarity	NPD5168	Approved
0.6186	Remote Similarity	NPD7115	Discovery
0.6186	Remote Similarity	NPD6317	Approved
0.6186	Remote Similarity	NPD6009	Approved
0.617	Remote Similarity	NPD6926	Approved
0.617	Remote Similarity	NPD6924	Approved
0.616	Remote Similarity	NPD7319	Approved
0.6134	Remote Similarity	NPD6313	Approved
0.6134	Remote Similarity	NPD6314	Approved
0.6129	Remote Similarity	NPD4243	Approved
0.6129	Remote Similarity	NPD8293	Discontinued
0.6126	Remote Similarity	NPD6052	Approved
0.6111	Remote Similarity	NPD7902	Approved
0.6106	Remote Similarity	NPD6412	Phase 2
0.6095	Remote Similarity	NPD7515	Phase 2
0.6083	Remote Similarity	NPD4522	Approved
0.6082	Remote Similarity	NPD4271	Approved
0.6082	Remote Similarity	NPD4268	Approved
0.608	Remote Similarity	NPD6033	Approved
0.6078	Remote Similarity	NPD4623	Approved
0.6078	Remote Similarity	NPD4519	Discontinued

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