NPASS Compound

Structure

NPC211352 OpenBabel07101718322D 30 34 0 0 1 0 0 0 0 0999 V2000 5.0372 4.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4062 3.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2757 4.8741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 4 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 18 2 0 0 0 0 6 19 2 0 0 0 0 7 11 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 26 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 23 1 1 0 0 0 20 26 1 0 0 0 0 21 24 1 1 0 0 0 21 26 1 0 0 0 0 22 24 1 1 0 0 0 22 25 1 0 0 0 0 23 1 1 6 0 0 0 24 2 1 1 0 0 0 25 3 1 1 0 0 0 25 30 1 0 0 0 0 26 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.28
Volume:	442.721
LogP:	4.581
LogD:	3.382
LogS:	-3.496
# Rotatable Bonds:	2
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	4.654
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.705
MDCK Permeability:	2.0733530618599616e-05
Pgp-inhibitor:	0.164
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.074
30% Bioavailability (F30%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421
Plasma Protein Binding (PPB):	90.91199493408203%
Volume Distribution (VD):	0.802
Pgp-substrate:	5.435094356536865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.388
CYP3A4-inhibitor:	0.97
CYP3A4-substrate:	0.512

ADMET: Excretion

Clearance (CL):	14.922
Half-life (T1/2):	0.474

ADMET: Toxicity

hERG Blockers:	0.203
Human Hepatotoxicity (H-HT):	0.683
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.628
Skin Sensitization:	0.94
Carcinogencity:	0.788
Eye Corrosion:	0.006
Eye Irritation:	0.035
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC211352

Natural Product ID:	NPC211352
*Common Name:**	LLYSRQZRILIUOI-NVDMUHRWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LLYSRQZRILIUOI-NVDMUHRWSA-N
Standard InCHI:	InChI=1S/C26H38O4/c1-23(15-27)9-4-10-26(16-28)20(23)7-11-24(2)21(26)8-12-25(3)22(24)14-17-13-18(29)5-6-19(17)30-25/h5-6,13,20-22,27-29H,4,7-12,14-16H2,1-3H3/t20-,21-,22-,23+,24+,25-,26+/m0/s1
SMILES:	C[C@@]1(CCC[C@@]2(CO)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@]2(C)[C@H]1Cc1cc(ccc1O2)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608574
PubChem CID:	11177475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO33273	strongylophora strongilata	Species	n.a.	n.a.	n.a.	Iriomote Island	n.a.	PMID[26253631]

☑ 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
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	14800.0	nM	PMID[520675]

☑ 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 NPC211352 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	417
0.1-0.2	1546
0.2-0.3	3226
0.3-0.4	7971
0.4-0.5	10349
0.5-0.6	6827
0.6-0.7	10352
0.7-0.8	1906
0.8-0.85	76
0.85-0.9	14
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC153019
0.9609	High Similarity	NPC27578
0.9609	High Similarity	NPC289624
0.9603	High Similarity	NPC47288
0.9545	High Similarity	NPC472794
0.9545	High Similarity	NPC473049
0.9328	High Similarity	NPC472791
0.9328	High Similarity	NPC472792
0.9286	High Similarity	NPC248557
0.9111	High Similarity	NPC76312
0.9048	High Similarity	NPC475839
0.903	High Similarity	NPC474610
0.8986	High Similarity	NPC474599
0.8971	High Similarity	NPC79372
0.8897	High Similarity	NPC265335
0.8864	High Similarity	NPC472793
0.874	High Similarity	NPC474131
0.8731	High Similarity	NPC85595
0.8712	High Similarity	NPC176590
0.8661	High Similarity	NPC32152
0.8661	High Similarity	NPC51341
0.8657	High Similarity	NPC473047
0.8652	High Similarity	NPC90645
0.8652	High Similarity	NPC472457
0.8615	High Similarity	NPC261992
0.8605	High Similarity	NPC168707
0.8605	High Similarity	NPC48623
0.8601	High Similarity	NPC212142
0.8594	High Similarity	NPC232295
0.8582	High Similarity	NPC196193
0.8582	High Similarity	NPC473048
0.8571	High Similarity	NPC186033
0.8561	High Similarity	NPC128321
0.855	High Similarity	NPC61685
0.8538	High Similarity	NPC46586
0.8538	High Similarity	NPC188997
0.8538	High Similarity	NPC204535
0.8527	High Similarity	NPC45663
0.8516	High Similarity	NPC471449
0.8504	High Similarity	NPC187993
0.8504	High Similarity	NPC238176
0.8496	Intermediate Similarity	NPC186889
0.8493	Intermediate Similarity	NPC325860
0.8485	Intermediate Similarity	NPC133407
0.8485	Intermediate Similarity	NPC28476
0.8483	Intermediate Similarity	NPC158784
0.8483	Intermediate Similarity	NPC195561
0.8478	Intermediate Similarity	NPC472800
0.8473	Intermediate Similarity	NPC474130
0.8467	Intermediate Similarity	NPC71372
0.8462	Intermediate Similarity	NPC471608
0.844	Intermediate Similarity	NPC323126
0.8429	Intermediate Similarity	NPC221134
0.8425	Intermediate Similarity	NPC302915
0.8425	Intermediate Similarity	NPC69539
0.8425	Intermediate Similarity	NPC141001
0.8425	Intermediate Similarity	NPC2745
0.8406	Intermediate Similarity	NPC279463
0.8382	Intermediate Similarity	NPC472590
0.837	Intermediate Similarity	NPC222108
0.837	Intermediate Similarity	NPC96719
0.837	Intermediate Similarity	NPC472797
0.8367	Intermediate Similarity	NPC157783
0.8321	Intermediate Similarity	NPC472798
0.8309	Intermediate Similarity	NPC249425
0.8309	Intermediate Similarity	NPC475880
0.8308	Intermediate Similarity	NPC135467
0.8308	Intermediate Similarity	NPC260832
0.8295	Intermediate Similarity	NPC283616
0.8295	Intermediate Similarity	NPC139047
0.8261	Intermediate Similarity	NPC469610
0.8261	Intermediate Similarity	NPC77196
0.8261	Intermediate Similarity	NPC138940
0.8258	Intermediate Similarity	NPC152946
0.8248	Intermediate Similarity	NPC474200
0.8248	Intermediate Similarity	NPC164804
0.8248	Intermediate Similarity	NPC244888
0.8248	Intermediate Similarity	NPC211413
0.8248	Intermediate Similarity	NPC118683
0.8248	Intermediate Similarity	NPC68205
0.8248	Intermediate Similarity	NPC293203
0.8248	Intermediate Similarity	NPC258073
0.8244	Intermediate Similarity	NPC129176
0.8244	Intermediate Similarity	NPC473875
0.8235	Intermediate Similarity	NPC93962
0.8235	Intermediate Similarity	NPC472796
0.8235	Intermediate Similarity	NPC472795
0.8214	Intermediate Similarity	NPC471522
0.8209	Intermediate Similarity	NPC76119
0.8209	Intermediate Similarity	NPC4286
0.8203	Intermediate Similarity	NPC473718
0.8201	Intermediate Similarity	NPC473107
0.8188	Intermediate Similarity	NPC469611
0.8175	Intermediate Similarity	NPC275627
0.8175	Intermediate Similarity	NPC77772
0.8169	Intermediate Similarity	NPC252901
0.8162	Intermediate Similarity	NPC53986
0.8162	Intermediate Similarity	NPC38604
0.8162	Intermediate Similarity	NPC211179
0.8162	Intermediate Similarity	NPC38664
0.8162	Intermediate Similarity	NPC223912
0.8156	Intermediate Similarity	NPC470307
0.8156	Intermediate Similarity	NPC470308
0.8148	Intermediate Similarity	NPC230479
0.8148	Intermediate Similarity	NPC283049
0.8148	Intermediate Similarity	NPC50315
0.8148	Intermediate Similarity	NPC26879
0.8146	Intermediate Similarity	NPC469507
0.8143	Intermediate Similarity	NPC327382
0.814	Intermediate Similarity	NPC126759
0.814	Intermediate Similarity	NPC242580
0.814	Intermediate Similarity	NPC236070
0.8134	Intermediate Similarity	NPC474237
0.8134	Intermediate Similarity	NPC276962
0.8134	Intermediate Similarity	NPC190086
0.8125	Intermediate Similarity	NPC471534
0.8121	Intermediate Similarity	NPC48671
0.812	Intermediate Similarity	NPC473464
0.812	Intermediate Similarity	NPC476332
0.8116	Intermediate Similarity	NPC474246
0.8116	Intermediate Similarity	NPC8899
0.8116	Intermediate Similarity	NPC474143
0.811	Intermediate Similarity	NPC177962
0.811	Intermediate Similarity	NPC62867
0.811	Intermediate Similarity	NPC98372
0.811	Intermediate Similarity	NPC474920
0.8106	Intermediate Similarity	NPC212559
0.8106	Intermediate Similarity	NPC96423
0.8102	Intermediate Similarity	NPC59654
0.8102	Intermediate Similarity	NPC271832
0.8102	Intermediate Similarity	NPC206028
0.8099	Intermediate Similarity	NPC19869
0.8099	Intermediate Similarity	NPC471388
0.8095	Intermediate Similarity	NPC473876
0.8092	Intermediate Similarity	NPC323074
0.8088	Intermediate Similarity	NPC473134
0.8085	Intermediate Similarity	NPC126101
0.8085	Intermediate Similarity	NPC141717
0.8085	Intermediate Similarity	NPC173660
0.8085	Intermediate Similarity	NPC327735
0.8085	Intermediate Similarity	NPC68292
0.8074	Intermediate Similarity	NPC124030
0.8074	Intermediate Similarity	NPC81641
0.8071	Intermediate Similarity	NPC476615
0.8071	Intermediate Similarity	NPC97834
0.8071	Intermediate Similarity	NPC311256
0.8071	Intermediate Similarity	NPC476616
0.8071	Intermediate Similarity	NPC184269
0.8071	Intermediate Similarity	NPC198154
0.8071	Intermediate Similarity	NPC115335
0.8071	Intermediate Similarity	NPC476617
0.8071	Intermediate Similarity	NPC225696
0.8071	Intermediate Similarity	NPC296915
0.8071	Intermediate Similarity	NPC223008
0.8069	Intermediate Similarity	NPC473845
0.8062	Intermediate Similarity	NPC301321
0.8058	Intermediate Similarity	NPC13005
0.8058	Intermediate Similarity	NPC189482
0.8058	Intermediate Similarity	NPC51262
0.8043	Intermediate Similarity	NPC325003
0.8043	Intermediate Similarity	NPC470727
0.8042	Intermediate Similarity	NPC174787
0.8042	Intermediate Similarity	NPC193920
0.8042	Intermediate Similarity	NPC164743
0.8042	Intermediate Similarity	NPC213607
0.8042	Intermediate Similarity	NPC182509
0.8041	Intermediate Similarity	NPC44452
0.8041	Intermediate Similarity	NPC476969
0.8031	Intermediate Similarity	NPC470770
0.8031	Intermediate Similarity	NPC266937
0.803	Intermediate Similarity	NPC325544
0.803	Intermediate Similarity	NPC477037
0.803	Intermediate Similarity	NPC318581
0.8029	Intermediate Similarity	NPC277458
0.8029	Intermediate Similarity	NPC307050
0.8029	Intermediate Similarity	NPC274717
0.8015	Intermediate Similarity	NPC470724
0.8015	Intermediate Similarity	NPC469609
0.8014	Intermediate Similarity	NPC23807
0.8014	Intermediate Similarity	NPC195022
0.8014	Intermediate Similarity	NPC11727
0.8014	Intermediate Similarity	NPC15109
0.8014	Intermediate Similarity	NPC125579
0.8014	Intermediate Similarity	NPC258780
0.8013	Intermediate Similarity	NPC188578
0.8013	Intermediate Similarity	NPC80918
0.8	Intermediate Similarity	NPC10154
0.8	Intermediate Similarity	NPC469663
0.8	Intermediate Similarity	NPC154256
0.8	Intermediate Similarity	NPC160196
0.8	Intermediate Similarity	NPC308828
0.8	Intermediate Similarity	NPC147896
0.8	Intermediate Similarity	NPC476452
0.8	Intermediate Similarity	NPC92
0.8	Intermediate Similarity	NPC92805
0.8	Intermediate Similarity	NPC227719
0.8	Intermediate Similarity	NPC290470
0.8	Intermediate Similarity	NPC265413
0.7987	Intermediate Similarity	NPC183380
0.7987	Intermediate Similarity	NPC477612

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 NPC211352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	881
0.2-0.3	1577
0.3-0.4	2655
0.4-0.5	1977
0.5-0.6	1072
0.6-0.7	557
0.7-0.8	85
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8492	Intermediate Similarity	NPD6671	Approved
0.8444	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD2861	Phase 2
0.8271	Intermediate Similarity	NPD6696	Suspended
0.8175	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD4908	Phase 1
0.814	Intermediate Similarity	NPD7340	Approved
0.8129	Intermediate Similarity	NPD5735	Approved
0.806	Intermediate Similarity	NPD5327	Phase 3
0.7971	Intermediate Similarity	NPD4625	Phase 3
0.7943	Intermediate Similarity	NPD6353	Approved
0.7929	Intermediate Similarity	NPD4140	Approved
0.7926	Intermediate Similarity	NPD4749	Approved
0.7907	Intermediate Similarity	NPD1398	Phase 1
0.7883	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD4060	Phase 1
0.7794	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD7157	Approved
0.7778	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7762	Intermediate Similarity	NPD7097	Phase 1
0.7754	Intermediate Similarity	NPD4624	Approved
0.774	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6674	Discontinued
0.7737	Intermediate Similarity	NPD8651	Approved
0.7704	Intermediate Similarity	NPD3496	Discontinued
0.7676	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3620	Phase 2
0.7638	Intermediate Similarity	NPD968	Approved
0.7612	Intermediate Similarity	NPD3091	Approved
0.7603	Intermediate Similarity	NPD5763	Approved
0.7603	Intermediate Similarity	NPD5762	Approved
0.76	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD7095	Approved
0.7569	Intermediate Similarity	NPD4097	Suspended
0.7568	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7635	Approved
0.7554	Intermediate Similarity	NPD3094	Phase 2
0.7552	Intermediate Similarity	NPD1613	Approved
0.7552	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7037	Approved
0.7518	Intermediate Similarity	NPD1611	Approved
0.7518	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD6584	Phase 3
0.7464	Intermediate Similarity	NPD2233	Approved
0.7464	Intermediate Similarity	NPD2232	Approved
0.7464	Intermediate Similarity	NPD2230	Approved
0.7436	Intermediate Similarity	NPD5929	Approved
0.7434	Intermediate Similarity	NPD6090	Discontinued
0.7434	Intermediate Similarity	NPD6273	Approved
0.7431	Intermediate Similarity	NPD2238	Phase 2
0.7424	Intermediate Similarity	NPD7843	Approved
0.7417	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7041	Phase 2
0.7413	Intermediate Similarity	NPD7985	Registered
0.7413	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7644	Approved
0.7394	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2684	Approved
0.7381	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD8127	Discontinued
0.7372	Intermediate Similarity	NPD4626	Approved
0.7372	Intermediate Similarity	NPD3095	Discontinued
0.7372	Intermediate Similarity	NPD1778	Approved
0.7368	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD8032	Phase 2
0.7353	Intermediate Similarity	NPD1548	Phase 1
0.7338	Intermediate Similarity	NPD2235	Phase 2
0.7338	Intermediate Similarity	NPD2231	Phase 2
0.7333	Intermediate Similarity	NPD8166	Discontinued
0.7333	Intermediate Similarity	NPD7003	Approved
0.7324	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5736	Approved
0.7299	Intermediate Similarity	NPD5691	Approved
0.7299	Intermediate Similarity	NPD5585	Approved
0.7292	Intermediate Similarity	NPD7294	Phase 1
0.729	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6583	Phase 3
0.7286	Intermediate Similarity	NPD6582	Phase 2
0.7279	Intermediate Similarity	NPD7119	Phase 2
0.726	Intermediate Similarity	NPD5124	Phase 1
0.726	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7447	Phase 1
0.7246	Intermediate Similarity	NPD4059	Approved
0.7239	Intermediate Similarity	NPD5283	Phase 1
0.7226	Intermediate Similarity	NPD7741	Discontinued
0.7222	Intermediate Similarity	NPD3027	Phase 3
0.7188	Intermediate Similarity	NPD7831	Phase 2
0.7188	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7833	Phase 2
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7176	Intermediate Similarity	NPD290	Approved
0.7164	Intermediate Similarity	NPD5535	Approved
0.7162	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4538	Approved
0.7162	Intermediate Similarity	NPD4536	Approved
0.716	Intermediate Similarity	NPD6959	Discontinued
0.7152	Intermediate Similarity	NPD5722	Discontinued
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD1091	Approved
0.7134	Intermediate Similarity	NPD27	Approved
0.7134	Intermediate Similarity	NPD2489	Approved
0.7133	Intermediate Similarity	NPD7030	Discontinued
0.7123	Intermediate Similarity	NPD6663	Approved
0.7122	Intermediate Similarity	NPD3019	Approved
0.7122	Intermediate Similarity	NPD6516	Phase 2
0.7122	Intermediate Similarity	NPD5846	Approved
0.7117	Intermediate Similarity	NPD3051	Approved
0.7108	Intermediate Similarity	NPD5844	Phase 1
0.7107	Intermediate Similarity	NPD8455	Phase 2
0.7101	Intermediate Similarity	NPD7311	Approved
0.7101	Intermediate Similarity	NPD7312	Approved
0.7101	Intermediate Similarity	NPD7310	Approved
0.7101	Intermediate Similarity	NPD7313	Approved
0.7095	Intermediate Similarity	NPD2157	Approved
0.7083	Intermediate Similarity	NPD1712	Approved
0.7083	Intermediate Similarity	NPD2237	Approved
0.7078	Intermediate Similarity	NPD7213	Phase 3
0.7078	Intermediate Similarity	NPD7212	Phase 2
0.7076	Intermediate Similarity	NPD4663	Approved
0.7075	Intermediate Similarity	NPD3110	Approved
0.7075	Intermediate Similarity	NPD3109	Approved
0.7073	Intermediate Similarity	NPD2970	Approved
0.7073	Intermediate Similarity	NPD2969	Approved
0.7067	Intermediate Similarity	NPD2935	Discontinued
0.7063	Intermediate Similarity	NPD4098	Discontinued
0.7063	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD2677	Approved
0.7059	Intermediate Similarity	NPD7309	Approved
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.705	Intermediate Similarity	NPD3443	Approved
0.705	Intermediate Similarity	NPD3445	Approved
0.705	Intermediate Similarity	NPD3444	Approved
0.7045	Intermediate Similarity	NPD2342	Discontinued
0.7042	Intermediate Similarity	NPD4359	Approved
0.7035	Intermediate Similarity	NPD7906	Approved
0.7031	Intermediate Similarity	NPD3020	Approved
0.7027	Intermediate Similarity	NPD3657	Discovery
0.7021	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2346	Discontinued
0.7014	Intermediate Similarity	NPD3690	Phase 2
0.7014	Intermediate Similarity	NPD3691	Phase 2
0.7013	Intermediate Similarity	NPD6667	Approved
0.7013	Intermediate Similarity	NPD6666	Approved
0.7012	Intermediate Similarity	NPD3787	Discontinued
0.7008	Intermediate Similarity	NPD288	Approved
0.7007	Intermediate Similarity	NPD7477	Discontinued
0.7007	Intermediate Similarity	NPD7265	Discontinued
0.7007	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD2932	Approved
0.7	Intermediate Similarity	NPD4108	Discontinued
0.7	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5588	Approved
0.7	Intermediate Similarity	NPD5960	Phase 3
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2668	Approved
0.7	Intermediate Similarity	NPD2667	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.6993	Remote Similarity	NPD1283	Approved
0.6993	Remote Similarity	NPD4110	Phase 3
0.6993	Remote Similarity	NPD4628	Phase 3
0.6993	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7466	Approved
0.6993	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3892	Phase 2
0.698	Remote Similarity	NPD6653	Approved
0.6974	Remote Similarity	NPD2424	Discontinued
0.6972	Remote Similarity	NPD1608	Approved
0.6963	Remote Similarity	NPD228	Approved
0.6959	Remote Similarity	NPD2979	Phase 3
0.6946	Remote Similarity	NPD7228	Approved
0.694	Remote Similarity	NPD5451	Approved
0.694	Remote Similarity	NPD3021	Approved
0.694	Remote Similarity	NPD3022	Approved
0.694	Remote Similarity	NPD4750	Phase 3
0.6939	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3268	Approved
0.6929	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1651	Approved
0.6929	Remote Similarity	NPD844	Approved
0.6929	Remote Similarity	NPD6382	Discontinued
0.6928	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3685	Discontinued
0.6914	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD7773	Phase 2
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD821	Approved
0.6908	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6002	Phase 3
0.6908	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6004	Phase 3
0.6908	Remote Similarity	NPD6005	Phase 3
0.6903	Remote Similarity	NPD5058	Phase 3
0.6903	Remote Similarity	NPD6815	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