NPASS Compound

Structure

NPC474250 OpenBabel07101718202D 31 37 0 0 1 0 0 0 0 0999 V2000 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -4.0000 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 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 1 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 1 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 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 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 21 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 13 1 1 6 0 0 0 13 14 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 17 11 1 6 0 0 0 17 18 1 0 0 0 0 18 25 1 1 0 0 0 19 13 1 1 0 0 0 19 30 1 0 0 0 0 20 12 1 1 0 0 0 20 23 1 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 27 2 0 0 0 0 22 26 1 6 0 0 0 22 31 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 1 0 0 0 24 28 1 1 0 0 0 24 30 1 0 0 0 0 25 26 1 1 0 0 0 26 9 1 1 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.21
Volume:	429.126
LogP:	3.848
LogD:	2.966
LogS:	-5.177
# Rotatable Bonds:	2
TPSA:	71.59
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	5.842
Fsp3:	0.654
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:	-4.777
MDCK Permeability:	2.567901356087532e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.502
30% Bioavailability (F30%):	0.42

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.742
Plasma Protein Binding (PPB):	91.46710968017578%
Volume Distribution (VD):	1.62
Pgp-substrate:	4.511472702026367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.863
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.236
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.772
CYP3A4-inhibitor:	0.779
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	13.555
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.975
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.539
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.481
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.719
Carcinogencity:	0.858
Eye Corrosion:	0.004
Eye Irritation:	0.083
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC474250

Natural Product ID:	NPC474250
*Common Name:**	Salpichrolide A
IUPAC Name:	n.a.
Synonyms:	Salpichrolide A
Standard InCHIKey:	MMZLVNBKAJDDJN-XZPDSABSSA-N
Standard InCHI:	InChI=1S/C26H30O5/c1-13(19-12-20-23(29-20)24(28)30-19)14-5-7-16-15(10-14)6-8-18-17(16)11-22-26(31-22)9-3-4-21(27)25(18,26)2/h3-5,7,10,13,17-20,22-24,28H,6,8-9,11-12H2,1-2H3/t13-,17-,18-,19-,20-,22-,23-,24+,25-,26-/m0/s1
SMILES:	C[C@@H](c1ccc2c(CC[C@H]3[C@H]2C[C@H]2[C@]4(CC=CC(=O)[C@]34C)O2)c1)[C@@H]1C[C@H]2[C@@H]([C@H](O)O1)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464196
PubChem CID:	44558900
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO2276	Salpichroa origanifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978207]
NPO2276	Salpichroa origanifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO2276	Salpichroa origanifolia	Species	Solanaceae	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
EC50	1
GI50	5
IC50	2
Others	7

Activity Type	# Activity
Cell Line	5
Individual Protein	1
NON-MOLECULAR	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	10.8	uM	PMID[476015]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	>	100000.0	nM	PMID[476016]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	9400.0	nM	PMID[476016]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	18000.0	nM	PMID[476016]
NPT134	Cell Line	SK-BR-3	Homo sapiens	GI50	>	100000.0	nM	PMID[476016]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	100.0	nM	PMID[476017]
NPT734	Organism	Musca domestica	Musca domestica	Activity	=	7.9	day	PMID[476014]
NPT734	Organism	Musca domestica	Musca domestica	Activity	=	10.3	day	PMID[476014]
NPT734	Organism	Musca domestica	Musca domestica	EC50	=	290.0	ppm	PMID[476014]
NPT734	Organism	Musca domestica	Musca domestica	Activity	=	6.9	day	PMID[476014]
NPT734	Organism	Musca domestica	Musca domestica	Activity	=	12.2	day	PMID[476014]
NPT734	Organism	Musca domestica	Musca domestica	Activity	=	100.0	%	PMID[476014]
NPT2	Others	Unspecified		Ratio	>	4.0	n.a.	PMID[476015]
NPT27	Others	Unspecified		IC50	>	42900.0	nM	PMID[476015]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	13000.0	nM	PMID[476016]

☑ 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 NPC474250 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	333
0.1-0.2	1187
0.2-0.3	2592
0.3-0.4	5764
0.4-0.5	10873
0.5-0.6	16433
0.6-0.7	5047
0.7-0.8	464
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9562	High Similarity	NPC474241
0.8912	High Similarity	NPC474501
0.7973	Intermediate Similarity	NPC111466
0.7919	Intermediate Similarity	NPC264270
0.7919	Intermediate Similarity	NPC40085
0.7895	Intermediate Similarity	NPC329657
0.7881	Intermediate Similarity	NPC470330
0.7871	Intermediate Similarity	NPC469417
0.7832	Intermediate Similarity	NPC80599
0.7832	Intermediate Similarity	NPC209851
0.7817	Intermediate Similarity	NPC262819
0.7792	Intermediate Similarity	NPC69425
0.7778	Intermediate Similarity	NPC159811
0.7762	Intermediate Similarity	NPC471334
0.7727	Intermediate Similarity	NPC472548
0.7718	Intermediate Similarity	NPC473755
0.7718	Intermediate Similarity	NPC475513
0.7712	Intermediate Similarity	NPC475417
0.7712	Intermediate Similarity	NPC475561
0.7712	Intermediate Similarity	NPC469448
0.7707	Intermediate Similarity	NPC469399
0.7703	Intermediate Similarity	NPC476643
0.7692	Intermediate Similarity	NPC27712
0.7692	Intermediate Similarity	NPC473443
0.7677	Intermediate Similarity	NPC133430
0.7677	Intermediate Similarity	NPC469477
0.7655	Intermediate Similarity	NPC144257
0.7654	Intermediate Similarity	NPC102465
0.7647	Intermediate Similarity	NPC81698
0.7647	Intermediate Similarity	NPC60509
0.7647	Intermediate Similarity	NPC250046
0.764	Intermediate Similarity	NPC477491
0.7639	Intermediate Similarity	NPC305162
0.7639	Intermediate Similarity	NPC472418
0.7635	Intermediate Similarity	NPC156393
0.7632	Intermediate Similarity	NPC469513
0.7628	Intermediate Similarity	NPC472549
0.7628	Intermediate Similarity	NPC5115
0.7625	Intermediate Similarity	NPC329960
0.7625	Intermediate Similarity	NPC150893
0.7625	Intermediate Similarity	NPC295408
0.7622	Intermediate Similarity	NPC225103
0.7613	Intermediate Similarity	NPC477905
0.7606	Intermediate Similarity	NPC171007
0.7606	Intermediate Similarity	NPC190849
0.7597	Intermediate Similarity	NPC161239
0.7597	Intermediate Similarity	NPC165260
0.7597	Intermediate Similarity	NPC198455
0.7597	Intermediate Similarity	NPC7095
0.7595	Intermediate Similarity	NPC477467
0.7595	Intermediate Similarity	NPC476784
0.7595	Intermediate Similarity	NPC3449
0.7594	Intermediate Similarity	NPC471189
0.7589	Intermediate Similarity	NPC244454
0.7582	Intermediate Similarity	NPC217918
0.7578	Intermediate Similarity	NPC471493
0.7569	Intermediate Similarity	NPC11025
0.7569	Intermediate Similarity	NPC472388
0.7568	Intermediate Similarity	NPC184109
0.7566	Intermediate Similarity	NPC277053
0.7566	Intermediate Similarity	NPC301946
0.7566	Intermediate Similarity	NPC127857
0.7564	Intermediate Similarity	NPC237549
0.7564	Intermediate Similarity	NPC472658
0.7564	Intermediate Similarity	NPC257213
0.7564	Intermediate Similarity	NPC146310
0.7564	Intermediate Similarity	NPC472022
0.7564	Intermediate Similarity	NPC472657
0.7564	Intermediate Similarity	NPC304876
0.7564	Intermediate Similarity	NPC1173
0.7564	Intermediate Similarity	NPC472005
0.7564	Intermediate Similarity	NPC242262
0.7564	Intermediate Similarity	NPC473414
0.7564	Intermediate Similarity	NPC249471
0.7564	Intermediate Similarity	NPC158333
0.7564	Intermediate Similarity	NPC472030
0.7564	Intermediate Similarity	NPC265395
0.7564	Intermediate Similarity	NPC256142
0.7562	Intermediate Similarity	NPC165234
0.7562	Intermediate Similarity	NPC475536
0.7552	Intermediate Similarity	NPC478162
0.7552	Intermediate Similarity	NPC478165
0.755	Intermediate Similarity	NPC477894
0.755	Intermediate Similarity	NPC91703
0.755	Intermediate Similarity	NPC477468
0.7548	Intermediate Similarity	NPC306799
0.7548	Intermediate Similarity	NPC101043
0.7546	Intermediate Similarity	NPC469420
0.7546	Intermediate Similarity	NPC478022
0.7546	Intermediate Similarity	NPC478020
0.7536	Intermediate Similarity	NPC476645
0.7535	Intermediate Similarity	NPC470818
0.7533	Intermediate Similarity	NPC77493
0.7532	Intermediate Similarity	NPC209393
0.7532	Intermediate Similarity	NPC477470
0.7532	Intermediate Similarity	NPC477474
0.7532	Intermediate Similarity	NPC205172
0.7532	Intermediate Similarity	NPC477472
0.7518	Intermediate Similarity	NPC77691
0.7516	Intermediate Similarity	NPC473641
0.7516	Intermediate Similarity	NPC473797
0.7516	Intermediate Similarity	NPC112523
0.7516	Intermediate Similarity	NPC228204
0.7516	Intermediate Similarity	NPC34066
0.7516	Intermediate Similarity	NPC471176
0.7516	Intermediate Similarity	NPC475437
0.7516	Intermediate Similarity	NPC26033
0.7516	Intermediate Similarity	NPC114410
0.7516	Intermediate Similarity	NPC475505
0.7516	Intermediate Similarity	NPC475300
0.7516	Intermediate Similarity	NPC475464
0.75	Intermediate Similarity	NPC369
0.75	Intermediate Similarity	NPC471912
0.75	Intermediate Similarity	NPC208651
0.75	Intermediate Similarity	NPC80895
0.75	Intermediate Similarity	NPC206641
0.75	Intermediate Similarity	NPC293831
0.75	Intermediate Similarity	NPC477488
0.7484	Intermediate Similarity	NPC174599
0.7484	Intermediate Similarity	NPC91730
0.7484	Intermediate Similarity	NPC82190
0.7484	Intermediate Similarity	NPC192219
0.7484	Intermediate Similarity	NPC112216
0.7483	Intermediate Similarity	NPC146239
0.7467	Intermediate Similarity	NPC477904
0.7467	Intermediate Similarity	NPC472547
0.7467	Intermediate Similarity	NPC100913
0.7467	Intermediate Similarity	NPC183270
0.7467	Intermediate Similarity	NPC275592
0.7466	Intermediate Similarity	NPC475493
0.7465	Intermediate Similarity	NPC317163
0.7453	Intermediate Similarity	NPC275477
0.7453	Intermediate Similarity	NPC53139
0.7452	Intermediate Similarity	NPC77719
0.745	Intermediate Similarity	NPC39549
0.7448	Intermediate Similarity	NPC49272
0.7447	Intermediate Similarity	NPC273336
0.7447	Intermediate Similarity	NPC182333
0.7438	Intermediate Similarity	NPC283480
0.7438	Intermediate Similarity	NPC148323
0.7436	Intermediate Similarity	NPC471103
0.7436	Intermediate Similarity	NPC197037
0.7432	Intermediate Similarity	NPC477896
0.7432	Intermediate Similarity	NPC23894
0.7432	Intermediate Similarity	NPC474659
0.7431	Intermediate Similarity	NPC195224
0.7423	Intermediate Similarity	NPC97637
0.7423	Intermediate Similarity	NPC187934
0.7421	Intermediate Similarity	NPC474621
0.7421	Intermediate Similarity	NPC474622
0.7421	Intermediate Similarity	NPC181924
0.7421	Intermediate Similarity	NPC469771
0.7419	Intermediate Similarity	NPC285122
0.7417	Intermediate Similarity	NPC213567
0.7417	Intermediate Similarity	NPC224491
0.7417	Intermediate Similarity	NPC97947
0.7417	Intermediate Similarity	NPC291599
0.7417	Intermediate Similarity	NPC118080
0.7417	Intermediate Similarity	NPC87448
0.7417	Intermediate Similarity	NPC41481
0.7417	Intermediate Similarity	NPC472576
0.7417	Intermediate Similarity	NPC27377
0.7415	Intermediate Similarity	NPC476644
0.7413	Intermediate Similarity	NPC470816
0.7413	Intermediate Similarity	NPC294050
0.7413	Intermediate Similarity	NPC328997
0.741	Intermediate Similarity	NPC202015
0.7407	Intermediate Similarity	NPC478073
0.7405	Intermediate Similarity	NPC471186
0.7405	Intermediate Similarity	NPC469422
0.7405	Intermediate Similarity	NPC469456
0.7397	Intermediate Similarity	NPC472361
0.7394	Intermediate Similarity	NPC477469
0.7394	Intermediate Similarity	NPC477471
0.7394	Intermediate Similarity	NPC469419
0.7394	Intermediate Similarity	NPC477473
0.7394	Intermediate Similarity	NPC477466
0.7386	Intermediate Similarity	NPC241951
0.7386	Intermediate Similarity	NPC475759
0.7386	Intermediate Similarity	NPC470152
0.7386	Intermediate Similarity	NPC475122
0.7383	Intermediate Similarity	NPC472551
0.7383	Intermediate Similarity	NPC472545
0.7375	Intermediate Similarity	NPC314257
0.7375	Intermediate Similarity	NPC49297
0.7372	Intermediate Similarity	NPC303429
0.7372	Intermediate Similarity	NPC222102
0.7368	Intermediate Similarity	NPC34012
0.7368	Intermediate Similarity	NPC63737
0.7368	Intermediate Similarity	NPC140021
0.7365	Intermediate Similarity	NPC469421
0.7365	Intermediate Similarity	NPC470580
0.7365	Intermediate Similarity	NPC478021
0.7362	Intermediate Similarity	NPC477627
0.7361	Intermediate Similarity	NPC253681
0.7361	Intermediate Similarity	NPC5486
0.7358	Intermediate Similarity	NPC474533
0.7358	Intermediate Similarity	NPC106895
0.7358	Intermediate Similarity	NPC474534
0.7357	Intermediate Similarity	NPC183339

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 NPC474250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	775
0.2-0.3	1792
0.3-0.4	3222
0.4-0.5	2100
0.5-0.6	835
0.6-0.7	136
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7388	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7799	Discontinued
0.7095	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3751	Discontinued
0.7006	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD7961	Discontinued
0.6994	Remote Similarity	NPD8313	Approved
0.6994	Remote Similarity	NPD8312	Approved
0.6993	Remote Similarity	NPD5126	Approved
0.6993	Remote Similarity	NPD5125	Phase 3
0.6954	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6858	Approved
0.6906	Remote Similarity	NPD7094	Approved
0.6905	Remote Similarity	NPD3787	Discontinued
0.6901	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7239	Suspended
0.6879	Remote Similarity	NPD3317	Approved
0.6833	Remote Similarity	NPD6535	Approved
0.6833	Remote Similarity	NPD6534	Approved
0.6809	Remote Similarity	NPD2629	Approved
0.6783	Remote Similarity	NPD7610	Discontinued
0.6782	Remote Similarity	NPD8368	Discontinued
0.678	Remote Similarity	NPD8150	Discontinued
0.6772	Remote Similarity	NPD8166	Discontinued
0.6738	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7700	Phase 2
0.6721	Remote Similarity	NPD7699	Phase 2
0.6712	Remote Similarity	NPD8328	Phase 3
0.6704	Remote Similarity	NPD8361	Approved
0.6704	Remote Similarity	NPD8435	Approved
0.6704	Remote Similarity	NPD8360	Approved
0.669	Remote Similarity	NPD5951	Approved
0.6685	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8407	Phase 2
0.6649	Remote Similarity	NPD6782	Approved
0.6649	Remote Similarity	NPD6777	Approved
0.6649	Remote Similarity	NPD6778	Approved
0.6649	Remote Similarity	NPD6781	Approved
0.6649	Remote Similarity	NPD6780	Approved
0.6649	Remote Similarity	NPD6776	Approved
0.6649	Remote Similarity	NPD6779	Approved
0.6646	Remote Similarity	NPD7458	Discontinued
0.6645	Remote Similarity	NPD7008	Discontinued
0.6644	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4198	Discontinued
0.6642	Remote Similarity	NPD2066	Phase 3
0.662	Remote Similarity	NPD6010	Discontinued
0.6605	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8320	Phase 1
0.6596	Remote Similarity	NPD8319	Approved
0.6593	Remote Similarity	NPD6212	Phase 3
0.6593	Remote Similarity	NPD6213	Phase 3
0.6593	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6823	Phase 2
0.6552	Remote Similarity	NPD7228	Approved
0.6543	Remote Similarity	NPD7435	Discontinued
0.6528	Remote Similarity	NPD7115	Discovery
0.6519	Remote Similarity	NPD5406	Approved
0.6519	Remote Similarity	NPD5405	Approved
0.6519	Remote Similarity	NPD5408	Approved
0.6519	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5404	Approved
0.6509	Remote Similarity	NPD7057	Phase 3
0.6509	Remote Similarity	NPD7058	Phase 2
0.6507	Remote Similarity	NPD7009	Phase 2
0.65	Remote Similarity	NPD6674	Discontinued
0.6497	Remote Similarity	NPD6559	Discontinued
0.6496	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1929	Approved
0.6496	Remote Similarity	NPD1930	Approved
0.6493	Remote Similarity	NPD3495	Discontinued
0.6488	Remote Similarity	NPD8455	Phase 2
0.6478	Remote Similarity	NPD2346	Discontinued
0.6475	Remote Similarity	NPD6412	Phase 2
0.6474	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7696	Phase 3
0.6455	Remote Similarity	NPD7697	Approved
0.6455	Remote Similarity	NPD7698	Approved
0.6447	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD37	Approved
0.6424	Remote Similarity	NPD7736	Approved
0.6421	Remote Similarity	NPD7870	Phase 2
0.6421	Remote Similarity	NPD7871	Phase 2
0.642	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6370	Approved
0.6414	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4965	Approved
0.6412	Remote Similarity	NPD4967	Phase 2
0.6412	Remote Similarity	NPD4966	Approved
0.6409	Remote Similarity	NPD8434	Phase 2
0.6407	Remote Similarity	NPD4380	Phase 2
0.6406	Remote Similarity	NPD7701	Phase 2
0.6405	Remote Similarity	NPD7084	Phase 3
0.6404	Remote Similarity	NPD7240	Approved
0.6402	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8485	Approved
0.6395	Remote Similarity	NPD7741	Discontinued
0.6392	Remote Similarity	NPD7801	Approved
0.6391	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1470	Approved
0.6375	Remote Similarity	NPD7266	Discontinued
0.6358	Remote Similarity	NPD4628	Phase 3
0.6358	Remote Similarity	NPD7003	Approved
0.6358	Remote Similarity	NPD8127	Discontinued
0.6357	Remote Similarity	NPD6685	Approved
0.6354	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6663	Approved
0.6341	Remote Similarity	NPD7390	Discontinued
0.634	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7874	Approved
0.6337	Remote Similarity	NPD6234	Discontinued
0.6328	Remote Similarity	NPD5844	Phase 1
0.631	Remote Similarity	NPD7028	Phase 2
0.6309	Remote Similarity	NPD2932	Approved
0.6309	Remote Similarity	NPD3019	Approved
0.6299	Remote Similarity	NPD5736	Approved
0.6292	Remote Similarity	NPD7074	Phase 3
0.6289	Remote Similarity	NPD7097	Phase 1
0.6286	Remote Similarity	NPD5048	Discontinued
0.6284	Remote Similarity	NPD6054	Approved
0.6277	Remote Similarity	NPD7798	Approved
0.6275	Remote Similarity	NPD3094	Phase 2
0.6268	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD4685	Phase 3
0.6266	Remote Similarity	NPD4684	Phase 3
0.6266	Remote Similarity	NPD4686	Approved
0.6265	Remote Similarity	NPD6273	Approved
0.6264	Remote Similarity	NPD6959	Discontinued
0.6259	Remote Similarity	NPD6647	Phase 2
0.6258	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3226	Approved
0.625	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7715	Approved
0.6242	Remote Similarity	NPD3614	Approved
0.6242	Remote Similarity	NPD2570	Approved
0.6242	Remote Similarity	NPD2573	Approved
0.6242	Remote Similarity	NPD3615	Approved
0.6242	Remote Similarity	NPD3616	Approved
0.6242	Remote Similarity	NPD2571	Approved
0.6242	Remote Similarity	NPD7714	Approved
0.6242	Remote Similarity	NPD3087	Approved
0.6242	Remote Similarity	NPD4745	Approved
0.6242	Remote Similarity	NPD6015	Approved
0.6242	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD3089	Approved
0.6242	Remote Similarity	NPD2574	Discontinued
0.6242	Remote Similarity	NPD4746	Phase 3
0.6242	Remote Similarity	NPD2566	Approved
0.6242	Remote Similarity	NPD3088	Approved
0.6242	Remote Similarity	NPD6016	Approved
0.6242	Remote Similarity	NPD3090	Approved
0.6236	Remote Similarity	NPD7054	Approved
0.6225	Remote Similarity	NPD1201	Approved
0.6222	Remote Similarity	NPD7685	Pre-registration
0.622	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6190	Approved
0.6215	Remote Similarity	NPD7473	Discontinued
0.6205	Remote Similarity	NPD8151	Discontinued
0.6205	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD7472	Approved
0.62	Remote Similarity	NPD5988	Approved
0.6199	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD7819	Suspended
0.6194	Remote Similarity	NPD1088	Approved
0.6187	Remote Similarity	NPD1932	Approved
0.6182	Remote Similarity	NPD3300	Phase 2
0.618	Remote Similarity	NPD3818	Discontinued
0.6176	Remote Similarity	NPD1989	Approved
0.6174	Remote Similarity	NPD6319	Approved
0.6173	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD7319	Approved
0.6167	Remote Similarity	NPD6797	Phase 2
0.6159	Remote Similarity	NPD3023	Approved
0.6159	Remote Similarity	NPD3026	Approved
0.6159	Remote Similarity	NPD4879	Approved
0.6159	Remote Similarity	NPD2575	Approved
0.6158	Remote Similarity	NPD8285	Discontinued
0.6154	Remote Similarity	NPD2329	Discontinued
0.6154	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2613	Approved
0.6149	Remote Similarity	NPD7305	Phase 1
0.6143	Remote Similarity	NPD5765	Approved
0.6142	Remote Similarity	NPD7783	Phase 2
0.6142	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6232	Discontinued
0.6133	Remote Similarity	NPD7251	Discontinued
0.6133	Remote Similarity	NPD3024	Approved
0.6133	Remote Similarity	NPD8517	Approved
0.6133	Remote Similarity	NPD8515	Approved
0.6133	Remote Similarity	NPD7503	Approved
0.6133	Remote Similarity	NPD8516	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