NPASS Compound

Structure

NPC205918 OpenBabel07101719242D 25 28 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 1.7321 2.0000 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 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 2 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 7 1 1 0 0 0 9 24 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 6 0 0 0 12 24 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 6 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 17 18 1 6 0 0 0 17 25 1 0 0 0 0 18 16 1 6 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.12
Volume:	334.008
LogP:	1.97
LogD:	0.574
LogS:	-2.467
# Rotatable Bonds:	4
TPSA:	116.59
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	4.618
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.832
MDCK Permeability:	1.340489870926831e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.706
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.706

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	72.54507446289062%
Volume Distribution (VD):	0.302
Pgp-substrate:	28.957534790039062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.146
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.59
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	8.092
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.724
Drug-inuced Liver Injury (DILI):	0.872
AMES Toxicity:	0.831
Rat Oral Acute Toxicity:	0.744
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.535
Carcinogencity:	0.832
Eye Corrosion:	0.003
Eye Irritation:	0.048
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC205918

Natural Product ID:	NPC205918
*Common Name:**	VMJVMTNZBQFQTG-VOYRUMQBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VMJVMTNZBQFQTG-VOYRUMQBSA-N
Standard InCHI:	InChI=1S/C18H20O7/c1-2-4-12-18-16(23)14-10(5-3-6-11(14)19)15(22)17(18,25-18)8-9(24-12)7-13(20)21/h3,5-6,9,12,15,19,22H,2,4,7-8H2,1H3,(H,20,21)/t9-,12-,15+,17-,18+/m1/s1
SMILES:	CCC[C@H]1O[C@H](CC(=O)O)C[C@@]23[C@@]1(O2)C(=O)c1c(O)cccc1[C@@H]3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409147
PubChem CID:	72191967
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO33097	Streptomyces sp. RM-4-15	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23944931]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	80000.0	nM	PMID[523730]

☑ 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 NPC205918 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	341
0.1-0.2	1291
0.2-0.3	2819
0.3-0.4	6337
0.4-0.5	10623
0.5-0.6	6735
0.6-0.7	7081
0.7-0.8	7136
0.8-0.85	294
0.85-0.9	34
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9589	High Similarity	NPC120171
0.9456	High Similarity	NPC280753
0.9456	High Similarity	NPC44378
0.9388	High Similarity	NPC94781
0.9145	High Similarity	NPC314257
0.8904	High Similarity	NPC114620
0.8904	High Similarity	NPC103337
0.8867	High Similarity	NPC285122
0.8867	High Similarity	NPC136878
0.8831	High Similarity	NPC312482
0.8805	High Similarity	NPC470735
0.8805	High Similarity	NPC329647
0.8782	High Similarity	NPC472889
0.8774	High Similarity	NPC170189
0.8774	High Similarity	NPC208173
0.8774	High Similarity	NPC3449
0.8766	High Similarity	NPC115249
0.8758	High Similarity	NPC56204
0.8733	High Similarity	NPC103910
0.8733	High Similarity	NPC29932
0.8726	High Similarity	NPC470339
0.871	High Similarity	NPC137301
0.8688	High Similarity	NPC472049
0.8681	High Similarity	NPC17843
0.8675	High Similarity	NPC170055
0.8675	High Similarity	NPC83272
0.8671	High Similarity	NPC472055
0.8667	High Similarity	NPC354984
0.8662	High Similarity	NPC206641
0.8662	High Similarity	NPC208651
0.8662	High Similarity	NPC246466
0.8654	High Similarity	NPC478133
0.8654	High Similarity	NPC317585
0.8654	High Similarity	NPC478230
0.8654	High Similarity	NPC69043
0.8645	High Similarity	NPC184284
0.8645	High Similarity	NPC478224
0.8645	High Similarity	NPC76041
0.8642	High Similarity	NPC473096
0.8642	High Similarity	NPC473095
0.8636	High Similarity	NPC475407
0.8636	High Similarity	NPC472891
0.8627	High Similarity	NPC470479
0.8616	High Similarity	NPC316457
0.8609	High Similarity	NPC300684
0.8609	High Similarity	NPC218866
0.8609	High Similarity	NPC48130
0.8609	High Similarity	NPC84568
0.859	High Similarity	NPC478231
0.859	High Similarity	NPC205172
0.859	High Similarity	NPC209393
0.8581	High Similarity	NPC197666
0.8581	High Similarity	NPC126739
0.858	High Similarity	NPC473094
0.858	High Similarity	NPC283041
0.8571	High Similarity	NPC474310
0.8535	High Similarity	NPC192219
0.8535	High Similarity	NPC99381
0.8535	High Similarity	NPC478221
0.8535	High Similarity	NPC174599
0.8535	High Similarity	NPC82190
0.8535	High Similarity	NPC472890
0.8533	High Similarity	NPC130485
0.8519	High Similarity	NPC20237
0.8506	High Similarity	NPC112816
0.8506	High Similarity	NPC142846
0.85	High Similarity	NPC478134
0.85	High Similarity	NPC317544
0.85	High Similarity	NPC117985
0.8497	Intermediate Similarity	NPC473023
0.8497	Intermediate Similarity	NPC63918
0.8497	Intermediate Similarity	NPC120536
0.8491	Intermediate Similarity	NPC314795
0.8481	Intermediate Similarity	NPC283480
0.8481	Intermediate Similarity	NPC148323
0.8481	Intermediate Similarity	NPC478027
0.8477	Intermediate Similarity	NPC308572
0.8471	Intermediate Similarity	NPC218870
0.8471	Intermediate Similarity	NPC182921
0.8471	Intermediate Similarity	NPC125487
0.8471	Intermediate Similarity	NPC474621
0.8471	Intermediate Similarity	NPC474824
0.8471	Intermediate Similarity	NPC281703
0.8471	Intermediate Similarity	NPC474622
0.8471	Intermediate Similarity	NPC470408
0.8466	Intermediate Similarity	NPC471295
0.8462	Intermediate Similarity	NPC215921
0.8462	Intermediate Similarity	NPC70016
0.8457	Intermediate Similarity	NPC191930
0.8456	Intermediate Similarity	NPC173980
0.8452	Intermediate Similarity	NPC208069
0.8447	Intermediate Similarity	NPC478229
0.8442	Intermediate Similarity	NPC81835
0.8428	Intermediate Similarity	NPC478225
0.8428	Intermediate Similarity	NPC29552
0.8424	Intermediate Similarity	NPC294501
0.8421	Intermediate Similarity	NPC21873
0.8421	Intermediate Similarity	NPC143898
0.8418	Intermediate Similarity	NPC471456
0.8411	Intermediate Similarity	NPC257003
0.8411	Intermediate Similarity	NPC244923
0.8408	Intermediate Similarity	NPC51824
0.8408	Intermediate Similarity	NPC268992
0.8408	Intermediate Similarity	NPC167903
0.8408	Intermediate Similarity	NPC113608
0.8408	Intermediate Similarity	NPC470338
0.8408	Intermediate Similarity	NPC470337
0.8403	Intermediate Similarity	NPC767
0.8403	Intermediate Similarity	NPC247250
0.84	Intermediate Similarity	NPC295339
0.8397	Intermediate Similarity	NPC469670
0.8397	Intermediate Similarity	NPC469619
0.8395	Intermediate Similarity	NPC249181
0.8378	Intermediate Similarity	NPC27407
0.8378	Intermediate Similarity	NPC142027
0.8377	Intermediate Similarity	NPC51513
0.8377	Intermediate Similarity	NPC472134
0.8377	Intermediate Similarity	NPC202112
0.8366	Intermediate Similarity	NPC151607
0.8366	Intermediate Similarity	NPC42540
0.8365	Intermediate Similarity	NPC474861
0.8365	Intermediate Similarity	NPC472050
0.8365	Intermediate Similarity	NPC164427
0.8364	Intermediate Similarity	NPC470580
0.8364	Intermediate Similarity	NPC478021
0.8355	Intermediate Similarity	NPC474300
0.8354	Intermediate Similarity	NPC471695
0.8354	Intermediate Similarity	NPC472211
0.8354	Intermediate Similarity	NPC478218
0.8344	Intermediate Similarity	NPC478022
0.8344	Intermediate Similarity	NPC158472
0.8344	Intermediate Similarity	NPC91809
0.8344	Intermediate Similarity	NPC478020
0.8333	Intermediate Similarity	NPC61590
0.8333	Intermediate Similarity	NPC237440
0.8333	Intermediate Similarity	NPC270160
0.8333	Intermediate Similarity	NPC4423
0.8333	Intermediate Similarity	NPC84142
0.8333	Intermediate Similarity	NPC77325
0.8333	Intermediate Similarity	NPC475974
0.8333	Intermediate Similarity	NPC478219
0.8323	Intermediate Similarity	NPC476463
0.8323	Intermediate Similarity	NPC215593
0.8323	Intermediate Similarity	NPC166583
0.8323	Intermediate Similarity	NPC53362
0.8323	Intermediate Similarity	NPC210320
0.8323	Intermediate Similarity	NPC472135
0.8323	Intermediate Similarity	NPC19056
0.8323	Intermediate Similarity	NPC470583
0.8313	Intermediate Similarity	NPC473113
0.8313	Intermediate Similarity	NPC183441
0.8313	Intermediate Similarity	NPC472620
0.8313	Intermediate Similarity	NPC270027
0.8313	Intermediate Similarity	NPC478226
0.8312	Intermediate Similarity	NPC474630
0.8312	Intermediate Similarity	NPC257558
0.8303	Intermediate Similarity	NPC328321
0.8302	Intermediate Similarity	NPC16082
0.8302	Intermediate Similarity	NPC82592
0.8302	Intermediate Similarity	NPC68727
0.8302	Intermediate Similarity	NPC175192
0.8301	Intermediate Similarity	NPC159721
0.8301	Intermediate Similarity	NPC471731
0.8301	Intermediate Similarity	NPC476473
0.8291	Intermediate Similarity	NPC478220
0.8291	Intermediate Similarity	NPC474534
0.8291	Intermediate Similarity	NPC321363
0.8291	Intermediate Similarity	NPC253904
0.8291	Intermediate Similarity	NPC295646
0.8291	Intermediate Similarity	NPC470340
0.8291	Intermediate Similarity	NPC180944
0.8291	Intermediate Similarity	NPC474533
0.8289	Intermediate Similarity	NPC472604
0.8289	Intermediate Similarity	NPC53649
0.8289	Intermediate Similarity	NPC472605
0.8289	Intermediate Similarity	NPC472603
0.828	Intermediate Similarity	NPC164762
0.8278	Intermediate Similarity	NPC476477
0.8278	Intermediate Similarity	NPC471602
0.8278	Intermediate Similarity	NPC299405
0.8278	Intermediate Similarity	NPC29771
0.8278	Intermediate Similarity	NPC306835
0.8278	Intermediate Similarity	NPC256463
0.8278	Intermediate Similarity	NPC216312
0.8278	Intermediate Similarity	NPC111422
0.8272	Intermediate Similarity	NPC112418
0.8272	Intermediate Similarity	NPC478222
0.8272	Intermediate Similarity	NPC477627
0.8269	Intermediate Similarity	NPC215711
0.8269	Intermediate Similarity	NPC73411
0.8267	Intermediate Similarity	NPC301915
0.8267	Intermediate Similarity	NPC474849
0.8267	Intermediate Similarity	NPC178467
0.8267	Intermediate Similarity	NPC474771
0.8267	Intermediate Similarity	NPC149372
0.8267	Intermediate Similarity	NPC261292
0.8267	Intermediate Similarity	NPC65837
0.8258	Intermediate Similarity	NPC229264
0.8258	Intermediate Similarity	NPC107625
0.825	Intermediate Similarity	NPC478223

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 NPC205918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	834
0.2-0.3	1635
0.3-0.4	2737
0.4-0.5	2066
0.5-0.6	1052
0.6-0.7	413
0.7-0.8	119
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.815	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD8150	Discontinued
0.8086	Intermediate Similarity	NPD7075	Discontinued
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6190	Approved
0.7901	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD7473	Discontinued
0.7853	Intermediate Similarity	NPD3817	Phase 2
0.784	Intermediate Similarity	NPD6801	Discontinued
0.784	Intermediate Similarity	NPD1934	Approved
0.7826	Intermediate Similarity	NPD4380	Phase 2
0.7811	Intermediate Similarity	NPD3751	Discontinued
0.7798	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6166	Phase 2
0.7798	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3787	Discontinued
0.7744	Intermediate Similarity	NPD5402	Approved
0.7736	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD2532	Approved
0.7736	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3300	Phase 2
0.7716	Intermediate Similarity	NPD6599	Discontinued
0.7705	Intermediate Similarity	NPD7435	Discontinued
0.7703	Intermediate Similarity	NPD1470	Approved
0.7697	Intermediate Similarity	NPD3882	Suspended
0.7674	Intermediate Similarity	NPD6797	Phase 2
0.7673	Intermediate Similarity	NPD6799	Approved
0.7671	Intermediate Similarity	NPD1201	Approved
0.7663	Intermediate Similarity	NPD8319	Approved
0.7663	Intermediate Similarity	NPD8320	Phase 1
0.7661	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5844	Phase 1
0.7654	Intermediate Similarity	NPD6534	Approved
0.7654	Intermediate Similarity	NPD6535	Approved
0.763	Intermediate Similarity	NPD7251	Discontinued
0.7625	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8434	Phase 2
0.759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7808	Phase 3
0.7582	Intermediate Similarity	NPD943	Approved
0.758	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2801	Approved
0.7564	Intermediate Similarity	NPD5404	Approved
0.7564	Intermediate Similarity	NPD5408	Approved
0.7564	Intermediate Similarity	NPD5406	Approved
0.7564	Intermediate Similarity	NPD5405	Approved
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3226	Approved
0.7545	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD8313	Approved
0.7543	Intermediate Similarity	NPD8312	Approved
0.7541	Intermediate Similarity	NPD6781	Approved
0.7541	Intermediate Similarity	NPD6780	Approved
0.7541	Intermediate Similarity	NPD6779	Approved
0.7541	Intermediate Similarity	NPD6777	Approved
0.7541	Intermediate Similarity	NPD6782	Approved
0.7541	Intermediate Similarity	NPD6776	Approved
0.7541	Intermediate Similarity	NPD6778	Approved
0.7531	Intermediate Similarity	NPD5403	Approved
0.7527	Intermediate Similarity	NPD7699	Phase 2
0.7527	Intermediate Similarity	NPD7700	Phase 2
0.7516	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD6959	Discontinued
0.7514	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1512	Approved
0.746	Intermediate Similarity	NPD7874	Approved
0.746	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7054	Approved
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6559	Discontinued
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7414	Intermediate Similarity	NPD7472	Approved
0.7407	Intermediate Similarity	NPD5401	Approved
0.7405	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1549	Phase 2
0.7353	Intermediate Similarity	NPD5494	Approved
0.7349	Intermediate Similarity	NPD7411	Suspended
0.7346	Intermediate Similarity	NPD1511	Approved
0.7342	Intermediate Similarity	NPD2935	Discontinued
0.7338	Intermediate Similarity	NPD3764	Approved
0.7337	Intermediate Similarity	NPD3749	Approved
0.7326	Intermediate Similarity	NPD7696	Phase 3
0.7326	Intermediate Similarity	NPD7697	Approved
0.7326	Intermediate Similarity	NPD7698	Approved
0.7321	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4954	Approved
0.7288	Intermediate Similarity	NPD5028	Approved
0.7288	Intermediate Similarity	NPD4955	Approved
0.7288	Intermediate Similarity	NPD36	Approved
0.7288	Intermediate Similarity	NPD5034	Approved
0.7288	Intermediate Similarity	NPD5026	Approved
0.7287	Intermediate Similarity	NPD7870	Phase 2
0.7287	Intermediate Similarity	NPD7871	Phase 2
0.7278	Intermediate Similarity	NPD1510	Phase 2
0.7267	Intermediate Similarity	NPD5710	Approved
0.7267	Intermediate Similarity	NPD5711	Approved
0.7263	Intermediate Similarity	NPD7701	Phase 2
0.7262	Intermediate Similarity	NPD1465	Phase 2
0.7249	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7685	Pre-registration
0.7232	Intermediate Similarity	NPD5030	Phase 2
0.7232	Intermediate Similarity	NPD8368	Discontinued
0.7222	Intermediate Similarity	NPD5037	Approved
0.7222	Intermediate Similarity	NPD5038	Approved
0.7205	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD37	Approved
0.7193	Intermediate Similarity	NPD6234	Discontinued
0.7184	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7236	Approved
0.7176	Intermediate Similarity	NPD4967	Phase 2
0.7176	Intermediate Similarity	NPD4966	Approved
0.7176	Intermediate Similarity	NPD4965	Approved
0.7167	Intermediate Similarity	NPD5036	Approved
0.716	Intermediate Similarity	NPD8166	Discontinued
0.716	Intermediate Similarity	NPD3750	Approved
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1607	Approved
0.7151	Intermediate Similarity	NPD5035	Approved
0.715	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7134	Intermediate Similarity	NPD1240	Approved
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2796	Approved
0.712	Intermediate Similarity	NPD6213	Phase 3
0.712	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6212	Phase 3
0.7111	Intermediate Similarity	NPD8407	Phase 2
0.7102	Intermediate Similarity	NPD7228	Approved
0.7093	Intermediate Similarity	NPD919	Approved
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6823	Phase 2
0.7085	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5762	Approved
0.7081	Intermediate Similarity	NPD7266	Discontinued
0.7081	Intermediate Similarity	NPD5763	Approved
0.7076	Intermediate Similarity	NPD7768	Phase 2
0.707	Intermediate Similarity	NPD6663	Approved
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2799	Discontinued
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD9545	Approved
0.7039	Intermediate Similarity	NPD9269	Phase 2
0.7032	Intermediate Similarity	NPD5736	Approved
0.7029	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6100	Approved
0.7019	Intermediate Similarity	NPD1551	Phase 2
0.7019	Intermediate Similarity	NPD6099	Approved
0.7013	Intermediate Similarity	NPD1164	Approved
0.7007	Intermediate Similarity	NPD2629	Approved
0.7006	Intermediate Similarity	NPD7799	Discontinued
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD2313	Discontinued
0.6981	Remote Similarity	NPD447	Suspended
0.6981	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7783	Phase 2
0.6964	Remote Similarity	NPD7239	Suspended
0.6957	Remote Similarity	NPD8435	Approved
0.6957	Remote Similarity	NPD8361	Approved
0.6957	Remote Similarity	NPD8360	Approved
0.6944	Remote Similarity	NPD5029	Approved
0.6944	Remote Similarity	NPD5027	Approved
0.6944	Remote Similarity	NPD5031	Approved
0.6928	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7458	Discontinued
0.6915	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1247	Approved
0.6914	Remote Similarity	NPD7199	Phase 2
0.6913	Remote Similarity	NPD9493	Approved
0.6897	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2800	Approved
0.6887	Remote Similarity	NPD9268	Approved
0.6871	Remote Similarity	NPD1471	Phase 3
0.6869	Remote Similarity	NPD7930	Approved
0.6859	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6233	Phase 2
0.6852	Remote Similarity	NPD3748	Approved
0.6851	Remote Similarity	NPD6765	Approved
0.6851	Remote Similarity	NPD6764	Approved
0.6848	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6273	Approved
0.6842	Remote Similarity	NPD3019	Approved
0.6842	Remote Similarity	NPD2932	Approved
0.6842	Remote Similarity	NPD8285	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