NPASS Compound

Structure

NPC211549 OpenBabel07101718322D 22 25 0 0 1 0 0 0 0 0999 V2000 2.8990 -2.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3010 2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 -2.3060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 -1.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 -1.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0330 0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1670 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0330 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 -1.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 -1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1670 0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3010 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 0.5243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3010 0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0576 -0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4631 -0.5398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8990 -1.4757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1670 1.5243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 -1.4757 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 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 8 1 1 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 8 1 1 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.1
Volume:	296.495
LogP:	3.235
LogD:	3.249
LogS:	-4.572
# Rotatable Bonds:	2
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.921
Synthetic Accessibility Score:	4.1
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	4.5829659939045087e-05
Pgp-inhibitor:	0.774
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	89.88130950927734%
Volume Distribution (VD):	0.607
Pgp-substrate:	12.849002838134766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.703
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.936
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.878
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.549
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.742

ADMET: Excretion

Clearance (CL):	12.788
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.585
Carcinogencity:	0.716
Eye Corrosion:	0.007
Eye Irritation:	0.885
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC211549

Natural Product ID:	NPC211549
*Common Name:**	PJAWURWFLOLDDW-WFASDCNBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PJAWURWFLOLDDW-WFASDCNBSA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-19-9-6-13(20-2)16-14(7-9)21-12-8-15(16)22-17-10(12)4-3-5-11(17)18/h3-7,12,15,18H,8H2,1-2H3/t12-,15-/m0/s1
SMILES:	COc1cc(OC)cc2c1[C@@H]1C[C@H](O2)c2c(O1)c(O)ccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1807888
PubChem CID:	46847424
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO8206	Iris tenuifolia	Species	Iridaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18472117]
NPO8206	Iris tenuifolia	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737268]
NPO8206	Iris tenuifolia	Species	Iridaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	19.8	%	PMID[463110]

☑ 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 NPC211549 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	442
0.1-0.2	1706
0.2-0.3	5201
0.3-0.4	12881
0.4-0.5	4639
0.5-0.6	4151
0.6-0.7	5872
0.7-0.8	5839
0.8-0.85	1076
0.85-0.9	616
0.9-0.95	224
0.95-1	50

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC112246
0.9846	High Similarity	NPC470356
0.9846	High Similarity	NPC121812
0.9846	High Similarity	NPC94750
0.9846	High Similarity	NPC112939
0.9846	High Similarity	NPC474206
0.9771	High Similarity	NPC227503
0.9771	High Similarity	NPC16435
0.9771	High Similarity	NPC230734
0.9771	High Similarity	NPC474639
0.9771	High Similarity	NPC306441
0.9697	High Similarity	NPC102904
0.9697	High Similarity	NPC103976
0.9697	High Similarity	NPC326797
0.9697	High Similarity	NPC474282
0.9697	High Similarity	NPC107551
0.9697	High Similarity	NPC176051
0.9695	High Similarity	NPC47398
0.9695	High Similarity	NPC61946
0.9695	High Similarity	NPC151224
0.9695	High Similarity	NPC260898
0.9695	High Similarity	NPC234333
0.9692	High Similarity	NPC11060
0.9621	High Similarity	NPC162659
0.9621	High Similarity	NPC248727
0.9621	High Similarity	NPC265433
0.9621	High Similarity	NPC302701
0.9621	High Similarity	NPC270456
0.9621	High Similarity	NPC269091
0.9618	High Similarity	NPC317380
0.9615	High Similarity	NPC86655
0.9615	High Similarity	NPC202762
0.9615	High Similarity	NPC127624
0.9559	High Similarity	NPC473108
0.9552	High Similarity	NPC309124
0.9552	High Similarity	NPC184797
0.9552	High Similarity	NPC22317
0.9549	High Similarity	NPC276490
0.9545	High Similarity	NPC164787
0.9545	High Similarity	NPC473413
0.9542	High Similarity	NPC168059
0.9542	High Similarity	NPC263064
0.9542	High Similarity	NPC475840
0.9542	High Similarity	NPC229442
0.9481	High Similarity	NPC471389
0.9478	High Similarity	NPC245207
0.9478	High Similarity	NPC127218
0.9478	High Similarity	NPC319647
0.9478	High Similarity	NPC70682
0.9478	High Similarity	NPC473739
0.9478	High Similarity	NPC232164
0.9478	High Similarity	NPC25966
0.9478	High Similarity	NPC260741
0.9478	High Similarity	NPC236306
0.9474	High Similarity	NPC472336
0.9474	High Similarity	NPC234952
0.9474	High Similarity	NPC470802
0.9474	High Similarity	NPC472334
0.947	High Similarity	NPC170694
0.9466	High Similarity	NPC185604
0.9466	High Similarity	NPC126029
0.9466	High Similarity	NPC61477
0.9466	High Similarity	NPC261619
0.9466	High Similarity	NPC201587
0.9466	High Similarity	NPC253105
0.9466	High Similarity	NPC219876
0.9466	High Similarity	NPC15658
0.9466	High Similarity	NPC78770
0.942	High Similarity	NPC125755
0.9416	High Similarity	NPC28440
0.9416	High Similarity	NPC171932
0.9412	High Similarity	NPC2613
0.9412	High Similarity	NPC59841
0.9412	High Similarity	NPC475891
0.9412	High Similarity	NPC107161
0.9412	High Similarity	NPC204347
0.9398	High Similarity	NPC472337
0.9398	High Similarity	NPC195022
0.9389	High Similarity	NPC42760
0.9389	High Similarity	NPC220825
0.9389	High Similarity	NPC472597
0.9389	High Similarity	NPC268342
0.9389	High Similarity	NPC268266
0.9353	High Similarity	NPC474397
0.9348	High Similarity	NPC277867
0.9348	High Similarity	NPC161700
0.9343	High Similarity	NPC81638
0.9338	High Similarity	NPC178054
0.9338	High Similarity	NPC35216
0.9338	High Similarity	NPC247291
0.9333	High Similarity	NPC32630
0.9333	High Similarity	NPC471388
0.9328	High Similarity	NPC173660
0.9323	High Similarity	NPC478085
0.9323	High Similarity	NPC106215
0.9318	High Similarity	NPC470752
0.9318	High Similarity	NPC35932
0.9318	High Similarity	NPC160991
0.9318	High Similarity	NPC7903
0.9318	High Similarity	NPC16208
0.9318	High Similarity	NPC184447
0.9313	High Similarity	NPC472338
0.9313	High Similarity	NPC91291
0.9308	High Similarity	NPC226331
0.9308	High Similarity	NPC31707
0.9308	High Similarity	NPC46274
0.9286	High Similarity	NPC473876
0.9286	High Similarity	NPC281549
0.9281	High Similarity	NPC233980
0.9275	High Similarity	NPC93323
0.9275	High Similarity	NPC12641
0.9275	High Similarity	NPC45257
0.9275	High Similarity	NPC469313
0.9275	High Similarity	NPC50250
0.9275	High Similarity	NPC168579
0.9275	High Similarity	NPC76176
0.9275	High Similarity	NPC138227
0.9275	High Similarity	NPC280092
0.9265	High Similarity	NPC160283
0.9265	High Similarity	NPC254759
0.9265	High Similarity	NPC259519
0.9265	High Similarity	NPC262189
0.9265	High Similarity	NPC27495
0.9259	High Similarity	NPC474390
0.9254	High Similarity	NPC134968
0.9242	High Similarity	NPC309787
0.9237	High Similarity	NPC170844
0.9237	High Similarity	NPC476968
0.9237	High Similarity	NPC210623
0.9237	High Similarity	NPC222004
0.9237	High Similarity	NPC86030
0.9237	High Similarity	NPC273295
0.9237	High Similarity	NPC285339
0.9237	High Similarity	NPC212015
0.9237	High Similarity	NPC226788
0.9237	High Similarity	NPC190629
0.9237	High Similarity	NPC3439
0.9237	High Similarity	NPC202582
0.9237	High Similarity	NPC218856
0.9237	High Similarity	NPC5851
0.9237	High Similarity	NPC470258
0.9231	High Similarity	NPC124452
0.9231	High Similarity	NPC282000
0.9231	High Similarity	NPC159968
0.9231	High Similarity	NPC246620
0.9231	High Similarity	NPC236791
0.9231	High Similarity	NPC293054
0.9231	High Similarity	NPC324112
0.9231	High Similarity	NPC210355
0.9231	High Similarity	NPC250432
0.9231	High Similarity	NPC169474
0.9231	High Similarity	NPC74817
0.9231	High Similarity	NPC5447
0.9231	High Similarity	NPC82679
0.922	High Similarity	NPC211561
0.9214	High Similarity	NPC101376
0.9214	High Similarity	NPC15538
0.9214	High Similarity	NPC21776
0.9214	High Similarity	NPC473480
0.9214	High Similarity	NPC16269
0.9209	High Similarity	NPC475096
0.9203	High Similarity	NPC37793
0.9203	High Similarity	NPC85264
0.9203	High Similarity	NPC47633
0.9203	High Similarity	NPC102044
0.9197	High Similarity	NPC265075
0.9197	High Similarity	NPC87725
0.9197	High Similarity	NPC263261
0.9191	High Similarity	NPC22517
0.9191	High Similarity	NPC292882
0.9179	High Similarity	NPC256307
0.9179	High Similarity	NPC66840
0.9179	High Similarity	NPC310854
0.9167	High Similarity	NPC311680
0.9167	High Similarity	NPC299221
0.9167	High Similarity	NPC234488
0.9167	High Similarity	NPC214860
0.9167	High Similarity	NPC51840
0.916	High Similarity	NPC222572
0.916	High Similarity	NPC206615
0.916	High Similarity	NPC252307
0.916	High Similarity	NPC470213
0.916	High Similarity	NPC245826
0.916	High Similarity	NPC98631
0.916	High Similarity	NPC72529
0.916	High Similarity	NPC474178
0.916	High Similarity	NPC186843
0.916	High Similarity	NPC87224
0.9154	High Similarity	NPC223136
0.9154	High Similarity	NPC28730
0.9154	High Similarity	NPC103823
0.9154	High Similarity	NPC214406
0.9154	High Similarity	NPC44748
0.9154	High Similarity	NPC18924
0.9154	High Similarity	NPC78974
0.9143	High Similarity	NPC99515
0.9143	High Similarity	NPC190714
0.9137	High Similarity	NPC63879
0.913	High Similarity	NPC475084
0.913	High Similarity	NPC189115

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 NPC211549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	898
0.2-0.3	1923
0.3-0.4	2734
0.4-0.5	1551
0.5-0.6	864
0.6-0.7	635
0.7-0.8	154
0.8-0.85	10
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9466	High Similarity	NPD1612	Clinical (unspecified phase)
0.9466	High Similarity	NPD1613	Approved
0.9308	High Similarity	NPD1529	Clinical (unspecified phase)
0.9237	High Similarity	NPD3027	Phase 3
0.9231	High Similarity	NPD1530	Clinical (unspecified phase)
0.8731	High Similarity	NPD4908	Phase 1
0.8603	High Similarity	NPD4907	Clinical (unspecified phase)
0.8581	High Similarity	NPD1934	Approved
0.8485	Intermediate Similarity	NPD1610	Phase 2
0.84	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6166	Phase 2
0.8387	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1548	Phase 1
0.8289	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD2861	Phase 2
0.8188	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8158	Intermediate Similarity	NPD2801	Approved
0.8129	Intermediate Similarity	NPD4625	Phase 3
0.8116	Intermediate Similarity	NPD3018	Phase 2
0.8113	Intermediate Similarity	NPD7054	Approved
0.8088	Intermediate Similarity	NPD4749	Approved
0.8063	Intermediate Similarity	NPD7472	Approved
0.7956	Intermediate Similarity	NPD2983	Phase 2
0.7956	Intermediate Similarity	NPD2982	Phase 2
0.7943	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3882	Suspended
0.7923	Intermediate Similarity	NPD228	Approved
0.7919	Intermediate Similarity	NPD1511	Approved
0.7901	Intermediate Similarity	NPD6797	Phase 2
0.7891	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6674	Discontinued
0.7883	Intermediate Similarity	NPD2981	Phase 2
0.7877	Intermediate Similarity	NPD7266	Discontinued
0.7853	Intermediate Similarity	NPD7251	Discontinued
0.7834	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7826	Intermediate Similarity	NPD7228	Approved
0.7815	Intermediate Similarity	NPD1512	Approved
0.781	Intermediate Similarity	NPD1091	Approved
0.7806	Intermediate Similarity	NPD1465	Phase 2
0.7805	Intermediate Similarity	NPD7808	Phase 3
0.7803	Intermediate Similarity	NPD5283	Phase 1
0.78	Intermediate Similarity	NPD7213	Phase 3
0.78	Intermediate Similarity	NPD7212	Phase 2
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5494	Approved
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7756	Intermediate Similarity	NPD3817	Phase 2
0.7748	Intermediate Similarity	NPD7447	Phase 1
0.7727	Intermediate Similarity	NPD4380	Phase 2
0.7708	Intermediate Similarity	NPD4060	Phase 1
0.7708	Intermediate Similarity	NPD1558	Phase 1
0.7698	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6671	Approved
0.7671	Intermediate Similarity	NPD4538	Approved
0.7671	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4536	Approved
0.7658	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD5124	Phase 1
0.7655	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1652	Phase 2
0.7635	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7619	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4678	Approved
0.7613	Intermediate Similarity	NPD4675	Approved
0.7605	Intermediate Similarity	NPD8053	Approved
0.7605	Intermediate Similarity	NPD8054	Approved
0.7595	Intermediate Similarity	NPD4966	Approved
0.7595	Intermediate Similarity	NPD4967	Phase 2
0.7595	Intermediate Similarity	NPD4965	Approved
0.7586	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3620	Phase 2
0.7584	Intermediate Similarity	NPD1549	Phase 2
0.7557	Intermediate Similarity	NPD2684	Approved
0.7554	Intermediate Similarity	NPD422	Phase 1
0.755	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7075	Discontinued
0.7533	Intermediate Similarity	NPD5177	Phase 3
0.7531	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD8651	Approved
0.7517	Intermediate Similarity	NPD3540	Phase 1
0.7516	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.7485	Intermediate Similarity	NPD7549	Discontinued
0.7481	Intermediate Similarity	NPD290	Approved
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7843	Approved
0.7455	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3539	Phase 1
0.745	Intermediate Similarity	NPD6099	Approved
0.745	Intermediate Similarity	NPD6100	Approved
0.7448	Intermediate Similarity	NPD6798	Discontinued
0.7438	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3705	Approved
0.7426	Intermediate Similarity	NPD7157	Approved
0.7421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6584	Phase 3
0.7413	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6959	Discontinued
0.7386	Intermediate Similarity	NPD5058	Phase 3
0.7368	Intermediate Similarity	NPD3750	Approved
0.7362	Intermediate Similarity	NPD6232	Discontinued
0.7355	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2796	Approved
0.7325	Intermediate Similarity	NPD4005	Discontinued
0.7324	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6559	Discontinued
0.7321	Intermediate Similarity	NPD7240	Approved
0.732	Intermediate Similarity	NPD2677	Approved
0.7312	Intermediate Similarity	NPD5402	Approved
0.7303	Intermediate Similarity	NPD3060	Approved
0.7297	Intermediate Similarity	NPD6355	Discontinued
0.729	Intermediate Similarity	NPD4123	Phase 3
0.729	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5846	Approved
0.7286	Intermediate Similarity	NPD6516	Phase 2
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD2489	Approved
0.7273	Intermediate Similarity	NPD968	Approved
0.7273	Intermediate Similarity	NPD27	Approved
0.7267	Intermediate Similarity	NPD7906	Approved
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD7095	Approved
0.7256	Intermediate Similarity	NPD3787	Discontinued
0.7255	Intermediate Similarity	NPD3892	Phase 2
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7466	Approved
0.7255	Intermediate Similarity	NPD6331	Phase 2
0.725	Intermediate Similarity	NPD7819	Suspended
0.725	Intermediate Similarity	NPD8455	Phase 2
0.7246	Intermediate Similarity	NPD8156	Discontinued
0.7237	Intermediate Similarity	NPD2424	Discontinued
0.7235	Intermediate Similarity	NPD4577	Approved
0.7235	Intermediate Similarity	NPD4578	Approved
0.7235	Intermediate Similarity	NPD7310	Approved
0.7235	Intermediate Similarity	NPD7313	Approved
0.7235	Intermediate Similarity	NPD7311	Approved
0.7235	Intermediate Similarity	NPD7312	Approved
0.7233	Intermediate Similarity	NPD7411	Suspended
0.7231	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.7229	Intermediate Similarity	NPD7473	Discontinued
0.7226	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6799	Approved
0.7226	Intermediate Similarity	NPD4357	Discontinued
0.7226	Intermediate Similarity	NPD1774	Approved
0.7214	Intermediate Similarity	NPD1357	Approved
0.7212	Intermediate Similarity	NPD2969	Approved
0.7212	Intermediate Similarity	NPD2970	Approved
0.7209	Intermediate Similarity	NPD4663	Approved
0.7208	Intermediate Similarity	NPD6190	Approved
0.7203	Intermediate Similarity	NPD6582	Phase 2
0.7203	Intermediate Similarity	NPD6583	Phase 3
0.72	Intermediate Similarity	NPD7097	Phase 1
0.7197	Intermediate Similarity	NPD5403	Approved
0.7197	Intermediate Similarity	NPD2122	Discontinued
0.7194	Intermediate Similarity	NPD5536	Phase 2
0.7193	Intermediate Similarity	NPD7309	Approved
0.7192	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4162	Approved
0.719	Intermediate Similarity	NPD4237	Approved
0.719	Intermediate Similarity	NPD4236	Phase 3
0.7188	Intermediate Similarity	NPD6801	Discontinued
0.7186	Intermediate Similarity	NPD8251	Approved
0.7186	Intermediate Similarity	NPD8252	Approved
0.7186	Intermediate Similarity	NPD8099	Discontinued
0.7181	Intermediate Similarity	NPD230	Phase 1
0.7181	Intermediate Similarity	NPD5735	Approved
0.7179	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5762	Approved
0.7171	Intermediate Similarity	NPD1375	Discontinued
0.7171	Intermediate Similarity	NPD5763	Approved
0.7161	Intermediate Similarity	NPD7124	Phase 2
0.716	Intermediate Similarity	NPD7768	Phase 2
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7152	Intermediate Similarity	NPD3051	Approved
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4535	Phase 3
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)

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