NPASS Compound

Structure

CID113428 OpenBabel06191715462D 26 27 0 0 1 0 0 0 0 0999 V2000 3.5594 2.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3784 4.5589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7906 5.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2083 6.0724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9771 3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5704 2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3893 4.3498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9716 3.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7961 5.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 2.5227 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3948 4.2453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1930 5.0543 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 -0.0119 3.3317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 20 2 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 25 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	380.155
LogP:	5.503
LogD:	4.489
LogS:	-4.058
# Rotatable Bonds:	8
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	3.462
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.608
MDCK Permeability:	1.7548241885378957e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.127
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	99.00910949707031%
Volume Distribution (VD):	2.201
Pgp-substrate:	3.546674966812134%

ADMET: Metabolism

CYP1A2-inhibitor:	0.837
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.777
CYP2D6-substrate:	0.541
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	14.028
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.743
Drug-inuced Liver Injury (DILI):	0.603
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.751
Skin Sensitization:	0.249
Carcinogencity:	0.132
Eye Corrosion:	0.004
Eye Irritation:	0.509
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC113428

Natural Product ID:	NPC113428
*Common Name:**	Shikonofuran C
IUPAC Name:	[1-[5-(2,5-dihydroxyphenyl)furan-3-yl]-4-methylpent-3-enyl] 3-methylbutanoate
Synonyms:	Shikonofuran C
Standard InCHIKey:	RQSVDMLEQSPRMK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-13(2)5-8-19(26-21(24)9-14(3)4)15-10-20(25-12-15)17-11-16(22)6-7-18(17)23/h5-7,10-12,14,19,22-23H,8-9H2,1-4H3
SMILES:	CC(CC(=O)OC(c1coc(c1)c1cc(O)ccc1O)CC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1946217
PubChem CID:	5321288
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000136] Hydroquinones

*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
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s11418-007-0221-0]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502328]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17157006]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19217780]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3373224]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7775984]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Ki	1
Others	1

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2228	Individual Protein	Neuraminidase	Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1))	IC50	>	100000.0	nM	PMID[547013]
NPT2	Others	Unspecified		IC50	=	20800.0	nM	PMID[547013]
NPT2	Others	Unspecified		Ki	=	150.0	nM	PMID[547013]
NPT2	Others	Unspecified		Kic	=	0.2	uM	PMID[547013]
NPT2	Others	Unspecified		IC50	=	600.0	nM	PMID[547013]

☑ 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 NPC113428 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	301
0.1-0.2	1384
0.2-0.3	3465
0.3-0.4	8637
0.4-0.5	10215
0.5-0.6	4010
0.6-0.7	6907
0.7-0.8	7445
0.8-0.85	316
0.85-0.9	14
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC61284
0.9929	High Similarity	NPC308799
0.8811	High Similarity	NPC278832
0.8811	High Similarity	NPC64157
0.8803	High Similarity	NPC265793
0.8645	High Similarity	NPC269495
0.8636	High Similarity	NPC474542
0.8621	High Similarity	NPC130976
0.8599	High Similarity	NPC24761
0.8571	High Similarity	NPC71525
0.8562	High Similarity	NPC98395
0.8542	High Similarity	NPC159786
0.8533	High Similarity	NPC98926
0.8467	Intermediate Similarity	NPC469642
0.8462	Intermediate Similarity	NPC7012
0.8452	Intermediate Similarity	NPC158261
0.8452	Intermediate Similarity	NPC290927
0.8452	Intermediate Similarity	NPC42458
0.8442	Intermediate Similarity	NPC170169
0.8421	Intermediate Similarity	NPC17816
0.8418	Intermediate Similarity	NPC169
0.8418	Intermediate Similarity	NPC49009
0.8408	Intermediate Similarity	NPC270044
0.8397	Intermediate Similarity	NPC198490
0.8389	Intermediate Similarity	NPC145673
0.8387	Intermediate Similarity	NPC207624
0.8387	Intermediate Similarity	NPC67654
0.8377	Intermediate Similarity	NPC155882
0.8377	Intermediate Similarity	NPC191104
0.8377	Intermediate Similarity	NPC167576
0.8377	Intermediate Similarity	NPC230713
0.8377	Intermediate Similarity	NPC78335
0.8366	Intermediate Similarity	NPC228012
0.8365	Intermediate Similarity	NPC14822
0.8364	Intermediate Similarity	NPC107244
0.8357	Intermediate Similarity	NPC4012
0.8355	Intermediate Similarity	NPC60389
0.8355	Intermediate Similarity	NPC211565
0.8354	Intermediate Similarity	NPC476350
0.8354	Intermediate Similarity	NPC477692
0.8354	Intermediate Similarity	NPC233956
0.8354	Intermediate Similarity	NPC476349
0.8344	Intermediate Similarity	NPC247677
0.8344	Intermediate Similarity	NPC10302
0.8344	Intermediate Similarity	NPC105381
0.8344	Intermediate Similarity	NPC89664
0.8344	Intermediate Similarity	NPC274085
0.8344	Intermediate Similarity	NPC160015
0.8333	Intermediate Similarity	NPC183874
0.8333	Intermediate Similarity	NPC329493
0.8333	Intermediate Similarity	NPC122365
0.8333	Intermediate Similarity	NPC141549
0.8323	Intermediate Similarity	NPC106372
0.8323	Intermediate Similarity	NPC23668
0.8323	Intermediate Similarity	NPC115324
0.8323	Intermediate Similarity	NPC58668
0.8323	Intermediate Similarity	NPC193976
0.8323	Intermediate Similarity	NPC156244
0.8323	Intermediate Similarity	NPC291110
0.8322	Intermediate Similarity	NPC477537
0.8312	Intermediate Similarity	NPC37226
0.8312	Intermediate Similarity	NPC178202
0.8312	Intermediate Similarity	NPC226644
0.8312	Intermediate Similarity	NPC88445
0.8302	Intermediate Similarity	NPC303210
0.8302	Intermediate Similarity	NPC95472
0.8302	Intermediate Similarity	NPC239270
0.8293	Intermediate Similarity	NPC247964
0.8291	Intermediate Similarity	NPC260902
0.8291	Intermediate Similarity	NPC296957
0.8289	Intermediate Similarity	NPC155144
0.828	Intermediate Similarity	NPC148938
0.8278	Intermediate Similarity	NPC476164
0.8278	Intermediate Similarity	NPC476310
0.8276	Intermediate Similarity	NPC470160
0.8276	Intermediate Similarity	NPC118253
0.8269	Intermediate Similarity	NPC183536
0.8269	Intermediate Similarity	NPC263676
0.8269	Intermediate Similarity	NPC142308
0.8269	Intermediate Similarity	NPC44606
0.8269	Intermediate Similarity	NPC253872
0.8269	Intermediate Similarity	NPC34965
0.8269	Intermediate Similarity	NPC281272
0.8264	Intermediate Similarity	NPC7569
0.8264	Intermediate Similarity	NPC278787
0.8264	Intermediate Similarity	NPC136340
0.8255	Intermediate Similarity	NPC18457
0.8255	Intermediate Similarity	NPC112757
0.8239	Intermediate Similarity	NPC40583
0.8239	Intermediate Similarity	NPC472877
0.8235	Intermediate Similarity	NPC469758
0.8232	Intermediate Similarity	NPC281835
0.8231	Intermediate Similarity	NPC176102
0.8231	Intermediate Similarity	NPC71108
0.8231	Intermediate Similarity	NPC204257
0.8231	Intermediate Similarity	NPC267539
0.8231	Intermediate Similarity	NPC254832
0.8231	Intermediate Similarity	NPC29317
0.8231	Intermediate Similarity	NPC229638
0.8228	Intermediate Similarity	NPC45131
0.8224	Intermediate Similarity	NPC302181
0.8219	Intermediate Similarity	NPC106247
0.8217	Intermediate Similarity	NPC477691
0.8217	Intermediate Similarity	NPC213608
0.8217	Intermediate Similarity	NPC235333
0.8217	Intermediate Similarity	NPC72370
0.8217	Intermediate Similarity	NPC470331
0.8217	Intermediate Similarity	NPC1477
0.8217	Intermediate Similarity	NPC472462
0.821	Intermediate Similarity	NPC136641
0.8205	Intermediate Similarity	NPC290671
0.8205	Intermediate Similarity	NPC116604
0.8205	Intermediate Similarity	NPC39819
0.82	Intermediate Similarity	NPC475044
0.82	Intermediate Similarity	NPC475063
0.82	Intermediate Similarity	NPC477535
0.8199	Intermediate Similarity	NPC84515
0.8199	Intermediate Similarity	NPC312056
0.8199	Intermediate Similarity	NPC193998
0.8194	Intermediate Similarity	NPC296030
0.8194	Intermediate Similarity	NPC317492
0.8194	Intermediate Similarity	NPC266499
0.8194	Intermediate Similarity	NPC39929
0.8193	Intermediate Similarity	NPC224165
0.8193	Intermediate Similarity	NPC53917
0.8187	Intermediate Similarity	NPC304839
0.8187	Intermediate Similarity	NPC115432
0.8187	Intermediate Similarity	NPC260296
0.8187	Intermediate Similarity	NPC220582
0.8182	Intermediate Similarity	NPC12148
0.8182	Intermediate Similarity	NPC304443
0.8182	Intermediate Similarity	NPC130581
0.8182	Intermediate Similarity	NPC150215
0.8182	Intermediate Similarity	NPC74539
0.8176	Intermediate Similarity	NPC212967
0.8176	Intermediate Similarity	NPC96342
0.8176	Intermediate Similarity	NPC473268
0.8176	Intermediate Similarity	NPC196448
0.8176	Intermediate Similarity	NPC246647
0.8176	Intermediate Similarity	NPC164110
0.817	Intermediate Similarity	NPC469764
0.817	Intermediate Similarity	NPC230943
0.8169	Intermediate Similarity	NPC4164
0.8165	Intermediate Similarity	NPC213936
0.8165	Intermediate Similarity	NPC297531
0.8165	Intermediate Similarity	NPC233776
0.8165	Intermediate Similarity	NPC99199
0.816	Intermediate Similarity	NPC277480
0.816	Intermediate Similarity	NPC155264
0.816	Intermediate Similarity	NPC67450
0.816	Intermediate Similarity	NPC193881
0.816	Intermediate Similarity	NPC210460
0.8158	Intermediate Similarity	NPC158871
0.8158	Intermediate Similarity	NPC472006
0.8158	Intermediate Similarity	NPC53192
0.8156	Intermediate Similarity	NPC477153
0.8153	Intermediate Similarity	NPC477690
0.8153	Intermediate Similarity	NPC215811
0.8153	Intermediate Similarity	NPC24232
0.8153	Intermediate Similarity	NPC5871
0.8153	Intermediate Similarity	NPC474843
0.8141	Intermediate Similarity	NPC37348
0.8141	Intermediate Similarity	NPC213382
0.8141	Intermediate Similarity	NPC475717
0.8141	Intermediate Similarity	NPC164527
0.8137	Intermediate Similarity	NPC45124
0.8137	Intermediate Similarity	NPC74854
0.8137	Intermediate Similarity	NPC269117
0.8137	Intermediate Similarity	NPC304387
0.8137	Intermediate Similarity	NPC30655
0.8137	Intermediate Similarity	NPC96031
0.8137	Intermediate Similarity	NPC188486
0.8133	Intermediate Similarity	NPC475045
0.8133	Intermediate Similarity	NPC475012
0.8133	Intermediate Similarity	NPC261471
0.8129	Intermediate Similarity	NPC55327
0.8129	Intermediate Similarity	NPC95526
0.8129	Intermediate Similarity	NPC37135
0.8129	Intermediate Similarity	NPC168085
0.8129	Intermediate Similarity	NPC135325
0.8129	Intermediate Similarity	NPC186397
0.8125	Intermediate Similarity	NPC226287
0.8125	Intermediate Similarity	NPC244750
0.8125	Intermediate Similarity	NPC196879
0.8125	Intermediate Similarity	NPC16935
0.8121	Intermediate Similarity	NPC131866
0.8121	Intermediate Similarity	NPC472376
0.8121	Intermediate Similarity	NPC477534
0.8117	Intermediate Similarity	NPC107625
0.8117	Intermediate Similarity	NPC300267
0.8117	Intermediate Similarity	NPC51641
0.8117	Intermediate Similarity	NPC472033
0.8117	Intermediate Similarity	NPC73320
0.8117	Intermediate Similarity	NPC299011
0.8117	Intermediate Similarity	NPC210826
0.8113	Intermediate Similarity	NPC180924
0.811	Intermediate Similarity	NPC472660
0.811	Intermediate Similarity	NPC86477
0.811	Intermediate Similarity	NPC247973
0.8108	Intermediate Similarity	NPC281513

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 NPC113428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	898
0.2-0.3	1602
0.3-0.4	2460
0.4-0.5	2063
0.5-0.6	1227
0.6-0.7	472
0.7-0.8	158
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8493	Intermediate Similarity	NPD2935	Discontinued
0.8435	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD920	Approved
0.8133	Intermediate Similarity	NPD6559	Discontinued
0.8121	Intermediate Similarity	NPD1551	Phase 2
0.8095	Intermediate Similarity	NPD447	Suspended
0.8085	Intermediate Similarity	NPD9717	Approved
0.8067	Intermediate Similarity	NPD2344	Approved
0.8054	Intermediate Similarity	NPD2799	Discontinued
0.8052	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5402	Approved
0.8042	Intermediate Similarity	NPD1203	Approved
0.8014	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD6832	Phase 2
0.7973	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2346	Discontinued
0.7922	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD411	Approved
0.7857	Intermediate Similarity	NPD2309	Approved
0.784	Intermediate Similarity	NPD3749	Approved
0.7821	Intermediate Similarity	NPD2533	Approved
0.7821	Intermediate Similarity	NPD2534	Approved
0.7821	Intermediate Similarity	NPD2532	Approved
0.7805	Intermediate Similarity	NPD1247	Approved
0.7792	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2801	Approved
0.7764	Intermediate Similarity	NPD7819	Suspended
0.7744	Intermediate Similarity	NPD5494	Approved
0.774	Intermediate Similarity	NPD1019	Discontinued
0.7736	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7075	Discontinued
0.7727	Intermediate Similarity	NPD1243	Approved
0.7714	Intermediate Similarity	NPD9493	Approved
0.7712	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1934	Approved
0.7692	Intermediate Similarity	NPD3496	Discontinued
0.7679	Intermediate Similarity	NPD3818	Discontinued
0.7671	Intermediate Similarity	NPD2797	Approved
0.7669	Intermediate Similarity	NPD7768	Phase 2
0.7662	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3268	Approved
0.7647	Intermediate Similarity	NPD2796	Approved
0.7643	Intermediate Similarity	NPD6799	Approved
0.764	Intermediate Similarity	NPD7411	Suspended
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3226	Approved
0.7619	Intermediate Similarity	NPD2798	Approved
0.761	Intermediate Similarity	NPD5403	Approved
0.7593	Intermediate Similarity	NPD6844	Discontinued
0.7582	Intermediate Similarity	NPD4308	Phase 3
0.7582	Intermediate Similarity	NPD1510	Phase 2
0.7564	Intermediate Similarity	NPD3750	Approved
0.7561	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1240	Approved
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5401	Approved
0.7469	Intermediate Similarity	NPD6599	Discontinued
0.7469	Intermediate Similarity	NPD4380	Phase 2
0.7457	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1607	Approved
0.744	Intermediate Similarity	NPD6808	Phase 2
0.7427	Intermediate Similarity	NPD5844	Phase 1
0.7421	Intermediate Similarity	NPD1511	Approved
0.7417	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7473	Discontinued
0.7389	Intermediate Similarity	NPD2800	Approved
0.7386	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7383	Intermediate Similarity	NPD5647	Approved
0.7381	Intermediate Similarity	NPD6959	Discontinued
0.7375	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6005	Phase 3
0.7372	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6004	Phase 3
0.7372	Intermediate Similarity	NPD6002	Phase 3
0.7372	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7033	Discontinued
0.7353	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6166	Phase 2
0.7353	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4628	Phase 3
0.7337	Intermediate Similarity	NPD6232	Discontinued
0.7329	Intermediate Similarity	NPD1512	Approved
0.7329	Intermediate Similarity	NPD6273	Approved
0.732	Intermediate Similarity	NPD4307	Phase 2
0.7315	Intermediate Similarity	NPD3266	Approved
0.7315	Intermediate Similarity	NPD3267	Approved
0.7314	Intermediate Similarity	NPD8312	Approved
0.7314	Intermediate Similarity	NPD8313	Approved
0.7303	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3926	Phase 2
0.7289	Intermediate Similarity	NPD2296	Approved
0.7283	Intermediate Similarity	NPD7074	Phase 3
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.7255	Intermediate Similarity	NPD6233	Phase 2
0.7244	Intermediate Similarity	NPD3748	Approved
0.7241	Intermediate Similarity	NPD5953	Discontinued
0.723	Intermediate Similarity	NPD1481	Phase 2
0.723	Intermediate Similarity	NPD1608	Approved
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7226	Intermediate Similarity	NPD6653	Approved
0.7225	Intermediate Similarity	NPD7054	Approved
0.7225	Intermediate Similarity	NPD7286	Phase 2
0.719	Intermediate Similarity	NPD6798	Discontinued
0.7186	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7472	Approved
0.7169	Intermediate Similarity	NPD6280	Approved
0.7169	Intermediate Similarity	NPD6279	Approved
0.7168	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1535	Discovery
0.7161	Intermediate Similarity	NPD230	Phase 1
0.7153	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1778	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD5711	Approved
0.7134	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7003	Approved
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9494	Approved
0.7105	Intermediate Similarity	NPD2861	Phase 2
0.7102	Intermediate Similarity	NPD7251	Discontinued
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7089	Intermediate Similarity	NPD6032	Approved
0.7086	Intermediate Similarity	NPD1164	Approved
0.7078	Intermediate Similarity	NPD3764	Approved
0.7075	Intermediate Similarity	NPD5585	Approved
0.7071	Intermediate Similarity	NPD9263	Approved
0.7071	Intermediate Similarity	NPD9267	Approved
0.7071	Intermediate Similarity	NPD9264	Approved
0.7062	Intermediate Similarity	NPD7808	Phase 3
0.7059	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4661	Approved
0.7055	Intermediate Similarity	NPD4662	Approved
0.7035	Intermediate Similarity	NPD7229	Phase 3
0.7027	Intermediate Similarity	NPD17	Approved
0.7024	Intermediate Similarity	NPD1465	Phase 2
0.702	Intermediate Similarity	NPD3225	Approved
0.702	Intermediate Similarity	NPD1283	Approved
0.7014	Intermediate Similarity	NPD1241	Discontinued
0.7007	Intermediate Similarity	NPD9545	Approved
0.7006	Intermediate Similarity	NPD5890	Approved
0.7006	Intermediate Similarity	NPD5889	Approved
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2424	Discontinued
0.6988	Remote Similarity	NPD7458	Discontinued
0.6987	Remote Similarity	NPD943	Approved
0.6987	Remote Similarity	NPD2979	Phase 3
0.6986	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5404	Approved
0.6981	Remote Similarity	NPD5405	Approved
0.6981	Remote Similarity	NPD5406	Approved
0.6981	Remote Similarity	NPD6099	Approved
0.6981	Remote Similarity	NPD6100	Approved
0.6981	Remote Similarity	NPD5408	Approved
0.6974	Remote Similarity	NPD1470	Approved
0.6974	Remote Similarity	NPD6362	Approved
0.6971	Remote Similarity	NPD3751	Discontinued
0.697	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD6234	Discontinued
0.6943	Remote Similarity	NPD4622	Approved
0.6943	Remote Similarity	NPD4618	Approved
0.6941	Remote Similarity	NPD4965	Approved
0.6941	Remote Similarity	NPD4967	Phase 2
0.6941	Remote Similarity	NPD4966	Approved
0.6933	Remote Similarity	NPD1611	Approved
0.6933	Remote Similarity	NPD7440	Discontinued
0.6933	Remote Similarity	NPD422	Phase 1
0.6923	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4287	Approved
0.6923	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3446	Phase 1
0.6914	Remote Similarity	NPD4110	Phase 3
0.6913	Remote Similarity	NPD4626	Approved
0.691	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1876	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