NPASS Compound

Structure

NPC472586 OpenBabel07101718292D 31 33 0 0 1 0 0 0 0 0999 V2000 -3.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 4.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 3.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2816 -0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7816 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0495 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7816 1.6488 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1835 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4811 4.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7816 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9756 3.1270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 2.1488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 -1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 0.1488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 23 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 2 1 1 0 0 0 13 21 1 0 0 0 0 13 25 1 0 0 0 0 14 19 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 17 12 1 1 0 0 0 17 22 1 0 0 0 0 17 26 1 0 0 0 0 18 24 1 0 0 0 0 18 28 1 1 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 25 2 0 0 0 0 22 30 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	427.25
Volume:	447.687
LogP:	3.058
LogD:	2.703
LogS:	-3.244
# Rotatable Bonds:	7
TPSA:	114.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	4.236
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.047
MDCK Permeability:	1.1130019629490562e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.916
Human Intestinal Absorption (HIA):	0.107
20% Bioavailability (F20%):	0.768
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233
Plasma Protein Binding (PPB):	74.00675201416016%
Volume Distribution (VD):	0.626
Pgp-substrate:	21.770343780517578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.287
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.542

ADMET: Excretion

Clearance (CL):	2.518
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.558
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.096
Carcinogencity:	0.112
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC472586

Natural Product ID:	NPC472586
*Common Name:**	PCQRMVOVGYONSH-KKXDTOCCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PCQRMVOVGYONSH-KKXDTOCCSA-N
Standard InCHI:	InChI=1S/C24H33N3O4/c1-7-23(3,4)20-16(12-17-22(30)25-13(2)21(29)26-17)15-10-8-9-14(19(15)27-20)11-18(28)24(5,6)31/h7-10,13,17-18,27-28,31H,1,11-12H2,2-6H3,(H,25,30)(H,26,29)/t13-,17-,18-/m0/s1
SMILES:	C=CC(c1[nH]c2c(c1C[C@@H]1N=C(O)[C@@H](N=C1O)C)cccc2C[C@@H](C(O)(C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577257
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids 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
NPO32640	eurotium rubrum ma-150	Species	Aspergillaceae	Eukaryota	Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.	n.a.	n.a.	PMID[25730346]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	16.5	uM	PMID[495387]

☑ 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 NPC472586 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	293
0.1-0.2	1498
0.2-0.3	10744
0.3-0.4	20396
0.4-0.5	4880
0.5-0.6	3041
0.6-0.7	1415
0.7-0.8	392
0.8-0.85	24
0.85-0.9	5
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC472443
0.963	High Similarity	NPC472444
0.9245	High Similarity	NPC470508
0.9207	High Similarity	NPC270009
0.9167	High Similarity	NPC207726
0.9114	High Similarity	NPC67056
0.8963	High Similarity	NPC34508
0.8916	High Similarity	NPC293472
0.8882	High Similarity	NPC16667
0.8868	High Similarity	NPC285469
0.8727	High Similarity	NPC280548
0.8671	High Similarity	NPC46413
0.8647	High Similarity	NPC192270
0.8485	Intermediate Similarity	NPC194640
0.8444	Intermediate Similarity	NPC32200
0.8438	Intermediate Similarity	NPC187951
0.8382	Intermediate Similarity	NPC19679
0.8344	Intermediate Similarity	NPC470507
0.8232	Intermediate Similarity	NPC38736
0.8225	Intermediate Similarity	NPC317430
0.821	Intermediate Similarity	NPC37548
0.8198	Intermediate Similarity	NPC288785
0.8166	Intermediate Similarity	NPC54988
0.8166	Intermediate Similarity	NPC474561
0.8166	Intermediate Similarity	NPC49954
0.8155	Intermediate Similarity	NPC40779
0.8144	Intermediate Similarity	NPC473320
0.814	Intermediate Similarity	NPC189812
0.814	Intermediate Similarity	NPC329688
0.8121	Intermediate Similarity	NPC471458
0.8118	Intermediate Similarity	NPC154293
0.8103	Intermediate Similarity	NPC133261
0.8095	Intermediate Similarity	NPC282231
0.8086	Intermediate Similarity	NPC129042
0.8072	Intermediate Similarity	NPC141353
0.8059	Intermediate Similarity	NPC160105
0.8047	Intermediate Similarity	NPC311276
0.8047	Intermediate Similarity	NPC472587
0.8036	Intermediate Similarity	NPC279918
0.8012	Intermediate Similarity	NPC201700
0.8012	Intermediate Similarity	NPC63751
0.8011	Intermediate Similarity	NPC314394
0.8	Intermediate Similarity	NPC470497
0.7989	Intermediate Similarity	NPC314957
0.7988	Intermediate Similarity	NPC124005
0.7977	Intermediate Similarity	NPC472123
0.7976	Intermediate Similarity	NPC230869
0.7967	Intermediate Similarity	NPC474177
0.7966	Intermediate Similarity	NPC472108
0.7966	Intermediate Similarity	NPC139291
0.7963	Intermediate Similarity	NPC242556
0.7944	Intermediate Similarity	NPC173028
0.7944	Intermediate Similarity	NPC65215
0.7943	Intermediate Similarity	NPC151939
0.7923	Intermediate Similarity	NPC133366
0.7917	Intermediate Similarity	NPC469762
0.7901	Intermediate Similarity	NPC95783
0.7892	Intermediate Similarity	NPC470499
0.7889	Intermediate Similarity	NPC317030
0.7889	Intermediate Similarity	NPC204565
0.788	Intermediate Similarity	NPC231342
0.7877	Intermediate Similarity	NPC163421
0.7877	Intermediate Similarity	NPC188387
0.7877	Intermediate Similarity	NPC62510
0.7874	Intermediate Similarity	NPC314603
0.7874	Intermediate Similarity	NPC97525
0.7865	Intermediate Similarity	NPC163055
0.7857	Intermediate Similarity	NPC184476
0.7857	Intermediate Similarity	NPC469785
0.7853	Intermediate Similarity	NPC300688
0.7853	Intermediate Similarity	NPC198339
0.7845	Intermediate Similarity	NPC34271
0.7833	Intermediate Similarity	NPC474707
0.7821	Intermediate Similarity	NPC165495
0.7821	Intermediate Similarity	NPC165201
0.7816	Intermediate Similarity	NPC6982
0.7816	Intermediate Similarity	NPC158129
0.7809	Intermediate Similarity	NPC302191
0.779	Intermediate Similarity	NPC119700
0.7784	Intermediate Similarity	NPC205403
0.7765	Intermediate Similarity	NPC469358
0.776	Intermediate Similarity	NPC243716
0.7742	Intermediate Similarity	NPC232130
0.774	Intermediate Similarity	NPC326575
0.774	Intermediate Similarity	NPC248454
0.774	Intermediate Similarity	NPC59269
0.7738	Intermediate Similarity	NPC259644
0.7738	Intermediate Similarity	NPC469760
0.7738	Intermediate Similarity	NPC469765
0.7738	Intermediate Similarity	NPC469763
0.7738	Intermediate Similarity	NPC469786
0.7738	Intermediate Similarity	NPC25008
0.7738	Intermediate Similarity	NPC73952
0.7735	Intermediate Similarity	NPC315555
0.7714	Intermediate Similarity	NPC470498
0.7709	Intermediate Similarity	NPC233936
0.7697	Intermediate Similarity	NPC72980
0.7692	Intermediate Similarity	NPC80597
0.7692	Intermediate Similarity	NPC211572
0.7692	Intermediate Similarity	NPC75540
0.7692	Intermediate Similarity	NPC212376
0.7692	Intermediate Similarity	NPC70922
0.768	Intermediate Similarity	NPC15102
0.7667	Intermediate Similarity	NPC472110
0.7667	Intermediate Similarity	NPC472109
0.7647	Intermediate Similarity	NPC229332
0.764	Intermediate Similarity	NPC68354
0.7629	Intermediate Similarity	NPC234999
0.7624	Intermediate Similarity	NPC472294
0.7617	Intermediate Similarity	NPC127677
0.7609	Intermediate Similarity	NPC314333
0.7584	Intermediate Similarity	NPC472122
0.7584	Intermediate Similarity	NPC24594
0.7584	Intermediate Similarity	NPC134586
0.7582	Intermediate Similarity	NPC476319
0.7565	Intermediate Similarity	NPC46225
0.7551	Intermediate Similarity	NPC151976
0.7547	Intermediate Similarity	NPC22079
0.7542	Intermediate Similarity	NPC211997
0.7541	Intermediate Similarity	NPC235684
0.7539	Intermediate Similarity	NPC476874
0.7539	Intermediate Similarity	NPC193761
0.7538	Intermediate Similarity	NPC475422
0.7529	Intermediate Similarity	NPC102423
0.7529	Intermediate Similarity	NPC271734
0.7528	Intermediate Similarity	NPC275305
0.7528	Intermediate Similarity	NPC37423
0.7526	Intermediate Similarity	NPC249040
0.7526	Intermediate Similarity	NPC87755
0.7525	Intermediate Similarity	NPC204491
0.7514	Intermediate Similarity	NPC71037
0.7514	Intermediate Similarity	NPC255229
0.7514	Intermediate Similarity	NPC469470
0.7514	Intermediate Similarity	NPC469501
0.7514	Intermediate Similarity	NPC81229
0.75	Intermediate Similarity	NPC477135
0.75	Intermediate Similarity	NPC219336
0.75	Intermediate Similarity	NPC88363
0.75	Intermediate Similarity	NPC299594
0.7473	Intermediate Similarity	NPC176127
0.7472	Intermediate Similarity	NPC313791
0.7462	Intermediate Similarity	NPC475778
0.7459	Intermediate Similarity	NPC175474
0.7459	Intermediate Similarity	NPC91179
0.7459	Intermediate Similarity	NPC187827
0.7459	Intermediate Similarity	NPC472105
0.745	Intermediate Similarity	NPC469594
0.7444	Intermediate Similarity	NPC217372
0.7444	Intermediate Similarity	NPC15573
0.7444	Intermediate Similarity	NPC183662
0.7436	Intermediate Similarity	NPC258062
0.7435	Intermediate Similarity	NPC79129
0.7435	Intermediate Similarity	NPC249150
0.7435	Intermediate Similarity	NPC49196
0.7435	Intermediate Similarity	NPC195461
0.7435	Intermediate Similarity	NPC313985
0.7435	Intermediate Similarity	NPC81654
0.7433	Intermediate Similarity	NPC67551
0.7432	Intermediate Similarity	NPC190007
0.7424	Intermediate Similarity	NPC469592
0.7424	Intermediate Similarity	NPC471080
0.7421	Intermediate Similarity	NPC50503
0.7421	Intermediate Similarity	NPC52557
0.7419	Intermediate Similarity	NPC106833
0.7419	Intermediate Similarity	NPC206967
0.7419	Intermediate Similarity	NPC329858
0.7419	Intermediate Similarity	NPC469497
0.7414	Intermediate Similarity	NPC131718
0.7409	Intermediate Similarity	NPC98715
0.7403	Intermediate Similarity	NPC213468
0.74	Intermediate Similarity	NPC79386
0.7399	Intermediate Similarity	NPC129721
0.7398	Intermediate Similarity	NPC271862
0.7396	Intermediate Similarity	NPC300183
0.7396	Intermediate Similarity	NPC475506
0.7391	Intermediate Similarity	NPC94943
0.7391	Intermediate Similarity	NPC475450
0.7391	Intermediate Similarity	NPC473189
0.7389	Intermediate Similarity	NPC267885
0.7385	Intermediate Similarity	NPC225821
0.7382	Intermediate Similarity	NPC100321
0.7381	Intermediate Similarity	NPC314372
0.7374	Intermediate Similarity	NPC87856
0.7366	Intermediate Similarity	NPC128751
0.7366	Intermediate Similarity	NPC213629
0.7366	Intermediate Similarity	NPC246700
0.7363	Intermediate Similarity	NPC15840
0.7363	Intermediate Similarity	NPC469896
0.736	Intermediate Similarity	NPC194411
0.7358	Intermediate Similarity	NPC155143
0.7358	Intermediate Similarity	NPC123019
0.735	Intermediate Similarity	NPC132211
0.735	Intermediate Similarity	NPC203614
0.7349	Intermediate Similarity	NPC2949
0.7344	Intermediate Similarity	NPC214428
0.7337	Intermediate Similarity	NPC84478
0.7337	Intermediate Similarity	NPC475602
0.7337	Intermediate Similarity	NPC267965
0.7333	Intermediate Similarity	NPC203468
0.7333	Intermediate Similarity	NPC110500

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 NPC472586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	519
0.2-0.3	758
0.3-0.4	1531
0.4-0.5	3242
0.5-0.6	2336
0.6-0.7	517
0.7-0.8	78
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
0.8208	Intermediate Similarity	NPD8386	Phase 2
0.807	Intermediate Similarity	NPD1325	Approved
0.807	Intermediate Similarity	NPD1326	Approved
0.7955	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6595	Phase 3
0.7705	Intermediate Similarity	NPD2564	Approved
0.7705	Intermediate Similarity	NPD2565	Phase 2
0.7697	Intermediate Similarity	NPD4079	Approved
0.7697	Intermediate Similarity	NPD4076	Approved
0.7692	Intermediate Similarity	NPD8431	Approved
0.7684	Intermediate Similarity	NPD2382	Approved
0.7684	Intermediate Similarity	NPD2381	Approved
0.7684	Intermediate Similarity	NPD2380	Approved
0.764	Intermediate Similarity	NPD3505	Approved
0.764	Intermediate Similarity	NPD3506	Approved
0.7609	Intermediate Similarity	NPD4499	Approved
0.7586	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5596	Phase 2
0.7542	Intermediate Similarity	NPD2144	Approved
0.7515	Intermediate Similarity	NPD1592	Phase 3
0.7513	Intermediate Similarity	NPD3003	Approved
0.75	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD2092	Phase 2
0.7473	Intermediate Similarity	NPD2095	Phase 2
0.7473	Intermediate Similarity	NPD2094	Phase 2
0.7459	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD4601	Approved
0.7435	Intermediate Similarity	NPD4600	Approved
0.7432	Intermediate Similarity	NPD2096	Phase 2
0.7432	Intermediate Similarity	NPD2091	Phase 2
0.7418	Intermediate Similarity	NPD3038	Discontinued
0.7412	Intermediate Similarity	NPD4462	Approved
0.7412	Intermediate Similarity	NPD4463	Approved
0.7405	Intermediate Similarity	NPD2383	Phase 1
0.7401	Intermediate Similarity	NPD4640	Approved
0.7401	Intermediate Similarity	NPD4638	Approved
0.7401	Intermediate Similarity	NPD4639	Approved
0.7401	Intermediate Similarity	NPD2844	Phase 3
0.7382	Intermediate Similarity	NPD1768	Approved
0.738	Intermediate Similarity	NPD5913	Phase 3
0.738	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7948	Phase 1
0.7368	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5003	Discontinued
0.7368	Intermediate Similarity	NPD6158	Phase 2
0.7348	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7957	Phase 1
0.7333	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5065	Approved
0.7333	Intermediate Similarity	NPD482	Approved
0.733	Intermediate Similarity	NPD5138	Approved
0.733	Intermediate Similarity	NPD5140	Approved
0.732	Intermediate Similarity	NPD2920	Discontinued
0.7303	Intermediate Similarity	NPD5021	Discontinued
0.7302	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4703	Approved
0.7294	Intermediate Similarity	NPD4702	Approved
0.7293	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3100	Discontinued
0.7219	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5254	Discontinued
0.7214	Intermediate Similarity	NPD5903	Approved
0.7214	Intermediate Similarity	NPD5902	Approved
0.7207	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8073	Approved
0.7173	Intermediate Similarity	NPD4602	Approved
0.7173	Intermediate Similarity	NPD7944	Discontinued
0.7168	Intermediate Similarity	NPD2882	Phase 1
0.716	Intermediate Similarity	NPD3525	Discontinued
0.7157	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8072	Approved
0.7127	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1392	Approved
0.7121	Intermediate Similarity	NPD8322	Phase 2
0.712	Intermediate Similarity	NPD1038	Approved
0.712	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2177	Approved
0.7113	Intermediate Similarity	NPD2176	Approved
0.7113	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2175	Phase 3
0.7113	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2172	Phase 1
0.7107	Intermediate Similarity	NPD8272	Phase 2
0.7107	Intermediate Similarity	NPD5901	Discontinued
0.7104	Intermediate Similarity	NPD5100	Phase 3
0.7094	Intermediate Similarity	NPD5612	Discontinued
0.7092	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD750	Phase 2
0.7083	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD786	Approved
0.7072	Intermediate Similarity	NPD7474	Suspended
0.7071	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8123	Approved
0.7065	Intermediate Similarity	NPD7470	Discontinued
0.7065	Intermediate Similarity	NPD8122	Approved
0.7059	Intermediate Similarity	NPD5164	Discontinued
0.7049	Intermediate Similarity	NPD6492	Phase 2
0.7047	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7935	Phase 2
0.7044	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4511	Phase 1
0.7037	Intermediate Similarity	NPD4948	Discontinued
0.7031	Intermediate Similarity	NPD802	Phase 2
0.702	Intermediate Similarity	NPD5426	Phase 3
0.7015	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7418	Discontinued
0.699	Remote Similarity	NPD4501	Approved
0.699	Remote Similarity	NPD4500	Approved
0.6989	Remote Similarity	NPD5899	Approved
0.6989	Remote Similarity	NPD6452	Discontinued
0.6989	Remote Similarity	NPD5897	Approved
0.6989	Remote Similarity	NPD5898	Approved
0.698	Remote Similarity	NPD5939	Approved
0.698	Remote Similarity	NPD5936	Approved
0.6974	Remote Similarity	NPD53	Approved
0.6974	Remote Similarity	NPD7778	Approved
0.6974	Remote Similarity	NPD7777	Approved
0.6973	Remote Similarity	NPD6159	Phase 2
0.6966	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3717	Discontinued
0.6957	Remote Similarity	NPD4128	Approved
0.6954	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6985	Discontinued
0.6939	Remote Similarity	NPD3814	Phase 1
0.6939	Remote Similarity	NPD6249	Phase 2
0.6939	Remote Similarity	NPD6248	Phase 2
0.6931	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6978	Phase 2
0.6919	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3835	Phase 3
0.6914	Remote Similarity	NPD3833	Phase 3
0.6911	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6455	Phase 3
0.6908	Remote Similarity	NPD7194	Discontinued
0.6907	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD484	Approved
0.6901	Remote Similarity	NPD1722	Approved
0.69	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5066	Phase 2
0.6897	Remote Similarity	NPD5067	Phase 2
0.6888	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6176	Phase 1
0.6875	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5255	Approved
0.6866	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4204	Approved
0.6862	Remote Similarity	NPD4203	Approved
0.686	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3961	Discontinued
0.6853	Remote Similarity	NPD8396	Approved
0.6853	Remote Similarity	NPD8395	Approved
0.6848	Remote Similarity	NPD3654	Approved
0.6845	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1683	Approved
0.6837	Remote Similarity	NPD7558	Phase 2
0.6832	Remote Similarity	NPD5658	Approved
0.6829	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4075	Phase 2
0.6825	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD1534	Approved
0.6814	Remote Similarity	NPD6220	Phase 3
0.6814	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5256	Discontinued
0.6804	Remote Similarity	NPD3404	Approved
0.6802	Remote Similarity	NPD7946	Pre-registration
0.6786	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3385	Approved
0.6782	Remote Similarity	NPD7453	Approved
0.6782	Remote Similarity	NPD7452	Approved
0.6782	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7222	Phase 2
0.678	Remote Similarity	NPD8093	Discontinued
0.678	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3330	Phase 1
0.6779	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2928	Phase 2

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