NPASS Compound

Structure

NPC472443 OpenBabel07101718322D 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 0 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 12 17 2 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 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:	425.23
Volume:	445.05
LogP:	2.878
LogD:	2.454
LogS:	-3.447
# Rotatable Bonds:	7
TPSA:	122.23
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	3.998
Fsp3:	0.417
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:	-5.247
MDCK Permeability:	1.3256792044558097e-05
Pgp-inhibitor:	0.904
Pgp-substrate:	0.798
Human Intestinal Absorption (HIA):	0.446
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	97.3537826538086%
Volume Distribution (VD):	0.336
Pgp-substrate:	2.5106186866760254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.555
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.405
CYP2C9-substrate:	0.483
CYP2D6-inhibitor:	0.324
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.637
CYP3A4-substrate:	0.781

ADMET: Excretion

Clearance (CL):	4.045
Half-life (T1/2):	0.744

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.71
Skin Sensitization:	0.134
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC472443

Natural Product ID:	NPC472443
*Common Name:**	BGZGVRPXCLBHLM-NRXXELKWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BGZGVRPXCLBHLM-NRXXELKWSA-N
Standard InCHI:	InChI=1S/C24H31N3O4/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/h7-10,12-13,18,27-28,31H,1,11H2,2-6H3,(H,25,30)(H,26,29)/b17-12-/t13-,18-/m0/s1
SMILES:	CC1C(=O)NC(=CC2=C(NC3=C(C=CC=C23)CC(C(C)(C)O)O)C(C)(C)C=C)C(=O)N1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3417728
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
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	200000.0	nM	PMID[534553]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	15.08	%	PMID[534553]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	2.4	uM	PMID[534554]

☑ 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 NPC472443 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	309
0.1-0.2	1495
0.2-0.3	10022
0.3-0.4	19955
0.4-0.5	5736
0.5-0.6	3161
0.6-0.7	1552
0.7-0.8	429
0.8-0.85	19
0.85-0.9	12
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC472444
0.9688	High Similarity	NPC472586
0.9509	High Similarity	NPC270009
0.9264	High Similarity	NPC34508
0.9212	High Similarity	NPC293472
0.8994	High Similarity	NPC207726
0.8957	High Similarity	NPC470508
0.8935	High Similarity	NPC192270
0.8844	High Similarity	NPC46413
0.8834	High Similarity	NPC16667
0.8827	High Similarity	NPC67056
0.882	High Similarity	NPC285469
0.8742	High Similarity	NPC187951
0.8642	High Similarity	NPC470507
0.8611	High Similarity	NPC32200
0.8571	High Similarity	NPC280548
0.8528	High Similarity	NPC38736
0.8509	High Similarity	NPC37548
0.848	Intermediate Similarity	NPC288785
0.8434	Intermediate Similarity	NPC473320
0.8415	Intermediate Similarity	NPC471458
0.8364	Intermediate Similarity	NPC141353
0.8343	Intermediate Similarity	NPC19679
0.8333	Intermediate Similarity	NPC194640
0.8286	Intermediate Similarity	NPC314394
0.8282	Intermediate Similarity	NPC124005
0.8272	Intermediate Similarity	NPC129042
0.8261	Intermediate Similarity	NPC242556
0.8225	Intermediate Similarity	NPC472587
0.8187	Intermediate Similarity	NPC317430
0.8129	Intermediate Similarity	NPC474561
0.8129	Intermediate Similarity	NPC49954
0.8129	Intermediate Similarity	NPC54988
0.8103	Intermediate Similarity	NPC189812
0.8103	Intermediate Similarity	NPC329688
0.8092	Intermediate Similarity	NPC6982
0.8092	Intermediate Similarity	NPC158129
0.8087	Intermediate Similarity	NPC133366
0.8081	Intermediate Similarity	NPC154293
0.8068	Intermediate Similarity	NPC133261
0.8059	Intermediate Similarity	NPC282231
0.8036	Intermediate Similarity	NPC184476
0.8033	Intermediate Similarity	NPC474177
0.8023	Intermediate Similarity	NPC198339
0.8012	Intermediate Similarity	NPC40779
0.8	Intermediate Similarity	NPC279918
0.7989	Intermediate Similarity	NPC470498
0.7977	Intermediate Similarity	NPC63751
0.7968	Intermediate Similarity	NPC470497
0.7966	Intermediate Similarity	NPC72980
0.7946	Intermediate Similarity	NPC205403
0.7943	Intermediate Similarity	NPC472123
0.7941	Intermediate Similarity	NPC230869
0.7933	Intermediate Similarity	NPC472108
0.7933	Intermediate Similarity	NPC139291
0.7919	Intermediate Similarity	NPC160105
0.7912	Intermediate Similarity	NPC34271
0.791	Intermediate Similarity	NPC151939
0.791	Intermediate Similarity	NPC326575
0.7907	Intermediate Similarity	NPC311276
0.7903	Intermediate Similarity	NPC232130
0.7874	Intermediate Similarity	NPC201700
0.7869	Intermediate Similarity	NPC95783
0.7865	Intermediate Similarity	NPC314957
0.7861	Intermediate Similarity	NPC470499
0.7857	Intermediate Similarity	NPC317030
0.7857	Intermediate Similarity	NPC204565
0.7845	Intermediate Similarity	NPC476319
0.7845	Intermediate Similarity	NPC163421
0.7845	Intermediate Similarity	NPC188387
0.7845	Intermediate Similarity	NPC62510
0.7833	Intermediate Similarity	NPC163055
0.7814	Intermediate Similarity	NPC65215
0.7814	Intermediate Similarity	NPC173028
0.7803	Intermediate Similarity	NPC271734
0.7803	Intermediate Similarity	NPC102423
0.7778	Intermediate Similarity	NPC302191
0.7778	Intermediate Similarity	NPC299594
0.7778	Intermediate Similarity	NPC469762
0.7778	Intermediate Similarity	NPC249040
0.7772	Intermediate Similarity	NPC127677
0.7765	Intermediate Similarity	NPC88363
0.7754	Intermediate Similarity	NPC231342
0.7753	Intermediate Similarity	NPC134586
0.7749	Intermediate Similarity	NPC477135
0.774	Intermediate Similarity	NPC313791
0.774	Intermediate Similarity	NPC314603
0.774	Intermediate Similarity	NPC97525
0.7735	Intermediate Similarity	NPC469358
0.7722	Intermediate Similarity	NPC300688
0.772	Intermediate Similarity	NPC46225
0.7719	Intermediate Similarity	NPC469785
0.7709	Intermediate Similarity	NPC211997
0.7709	Intermediate Similarity	NPC59269
0.7709	Intermediate Similarity	NPC248454
0.7705	Intermediate Similarity	NPC315555
0.7705	Intermediate Similarity	NPC474707
0.7704	Intermediate Similarity	NPC151976
0.7692	Intermediate Similarity	NPC190007
0.7692	Intermediate Similarity	NPC165201
0.7692	Intermediate Similarity	NPC165495
0.7692	Intermediate Similarity	NPC475422
0.7688	Intermediate Similarity	NPC469594
0.7688	Intermediate Similarity	NPC131718
0.768	Intermediate Similarity	NPC233936
0.7677	Intermediate Similarity	NPC204491
0.7665	Intermediate Similarity	NPC471080
0.7665	Intermediate Similarity	NPC469592
0.7663	Intermediate Similarity	NPC119700
0.765	Intermediate Similarity	NPC94943
0.765	Intermediate Similarity	NPC15102
0.7637	Intermediate Similarity	NPC472109
0.7637	Intermediate Similarity	NPC176127
0.7637	Intermediate Similarity	NPC472110
0.7634	Intermediate Similarity	NPC243716
0.7622	Intermediate Similarity	NPC246700
0.7622	Intermediate Similarity	NPC128751
0.7611	Intermediate Similarity	NPC68354
0.7602	Intermediate Similarity	NPC234999
0.7602	Intermediate Similarity	NPC73952
0.7602	Intermediate Similarity	NPC469765
0.7602	Intermediate Similarity	NPC469760
0.7602	Intermediate Similarity	NPC469763
0.7602	Intermediate Similarity	NPC25008
0.7602	Intermediate Similarity	NPC259644
0.7602	Intermediate Similarity	NPC469786
0.76	Intermediate Similarity	NPC476118
0.759	Intermediate Similarity	NPC87755
0.759	Intermediate Similarity	NPC258062
0.7581	Intermediate Similarity	NPC206967
0.7581	Intermediate Similarity	NPC469497
0.7581	Intermediate Similarity	NPC314333
0.7581	Intermediate Similarity	NPC106833
0.7579	Intermediate Similarity	NPC306376
0.7577	Intermediate Similarity	NPC476106
0.7569	Intermediate Similarity	NPC176199
0.7569	Intermediate Similarity	NPC215795
0.7565	Intermediate Similarity	NPC98715
0.7558	Intermediate Similarity	NPC70922
0.7558	Intermediate Similarity	NPC212376
0.7558	Intermediate Similarity	NPC80597
0.7558	Intermediate Similarity	NPC211572
0.7558	Intermediate Similarity	NPC75540
0.7556	Intermediate Similarity	NPC472122
0.7556	Intermediate Similarity	NPC24594
0.7554	Intermediate Similarity	NPC314002
0.7554	Intermediate Similarity	NPC473189
0.7552	Intermediate Similarity	NPC300183
0.7551	Intermediate Similarity	NPC271862
0.7542	Intermediate Similarity	NPC474409
0.7541	Intermediate Similarity	NPC48938
0.7541	Intermediate Similarity	NPC212535
0.7538	Intermediate Similarity	NPC225821
0.7526	Intermediate Similarity	NPC229332
0.7525	Intermediate Similarity	NPC87856
0.7516	Intermediate Similarity	NPC22079
0.7514	Intermediate Similarity	NPC235684
0.7514	Intermediate Similarity	NPC171171
0.7513	Intermediate Similarity	NPC276517
0.75	Intermediate Similarity	NPC275305
0.75	Intermediate Similarity	NPC84478
0.75	Intermediate Similarity	NPC132211
0.75	Intermediate Similarity	NPC472294
0.75	Intermediate Similarity	NPC203614
0.75	Intermediate Similarity	NPC37423
0.75	Intermediate Similarity	NPC61637
0.75	Intermediate Similarity	NPC204717
0.75	Intermediate Similarity	NPC99666
0.7487	Intermediate Similarity	NPC469501
0.7487	Intermediate Similarity	NPC469470
0.7487	Intermediate Similarity	NPC267965
0.7486	Intermediate Similarity	NPC71037
0.7486	Intermediate Similarity	NPC81229
0.7486	Intermediate Similarity	NPC255229
0.7485	Intermediate Similarity	NPC105818
0.7485	Intermediate Similarity	NPC24678
0.7473	Intermediate Similarity	NPC219336
0.7473	Intermediate Similarity	NPC46580
0.7463	Intermediate Similarity	NPC141428
0.7459	Intermediate Similarity	NPC203754
0.7459	Intermediate Similarity	NPC150048
0.7449	Intermediate Similarity	NPC244741
0.7448	Intermediate Similarity	NPC128823
0.7446	Intermediate Similarity	NPC220765
0.7437	Intermediate Similarity	NPC475778
0.7435	Intermediate Similarity	NPC70956
0.7435	Intermediate Similarity	NPC153042
0.7435	Intermediate Similarity	NPC243834
0.7433	Intermediate Similarity	NPC175474
0.7432	Intermediate Similarity	NPC472105
0.7432	Intermediate Similarity	NPC187827
0.7432	Intermediate Similarity	NPC91179
0.7424	Intermediate Similarity	NPC5145
0.7423	Intermediate Similarity	NPC476874
0.7423	Intermediate Similarity	NPC193761
0.7423	Intermediate Similarity	NPC123019
0.7421	Intermediate Similarity	NPC195314
0.7418	Intermediate Similarity	NPC15573
0.7418	Intermediate Similarity	NPC183662
0.7418	Intermediate Similarity	NPC217372

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 NPC472443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	527
0.2-0.3	757
0.3-0.4	1453
0.4-0.5	3089
0.5-0.6	2459
0.6-0.7	592
0.7-0.8	101
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
0.8353	Intermediate Similarity	NPD1325	Approved
0.8353	Intermediate Similarity	NPD1326	Approved
0.7966	Intermediate Similarity	NPD8386	Phase 2
0.7955	Intermediate Similarity	NPD2380	Approved
0.7955	Intermediate Similarity	NPD2382	Approved
0.7955	Intermediate Similarity	NPD2381	Approved
0.7833	Intermediate Similarity	NPD5596	Phase 2
0.7829	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1592	Phase 3
0.7778	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD2564	Approved
0.7772	Intermediate Similarity	NPD2565	Phase 2
0.7722	Intermediate Similarity	NPD6595	Phase 3
0.7692	Intermediate Similarity	NPD4463	Approved
0.7692	Intermediate Similarity	NPD4462	Approved
0.767	Intermediate Similarity	NPD2844	Phase 3
0.7668	Intermediate Similarity	NPD3003	Approved
0.7667	Intermediate Similarity	NPD4076	Approved
0.7667	Intermediate Similarity	NPD4079	Approved
0.7663	Intermediate Similarity	NPD2383	Phase 1
0.7647	Intermediate Similarity	NPD6158	Phase 2
0.7647	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD3506	Approved
0.7611	Intermediate Similarity	NPD3505	Approved
0.76	Intermediate Similarity	NPD5140	Approved
0.76	Intermediate Similarity	NPD5138	Approved
0.7598	Intermediate Similarity	NPD5065	Approved
0.7581	Intermediate Similarity	NPD4499	Approved
0.7568	Intermediate Similarity	NPD8431	Approved
0.7553	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5913	Phase 3
0.7539	Intermediate Similarity	NPD1768	Approved
0.7526	Intermediate Similarity	NPD5003	Discontinued
0.7526	Intermediate Similarity	NPD7948	Phase 1
0.7514	Intermediate Similarity	NPD2144	Approved
0.7473	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD2092	Phase 2
0.7446	Intermediate Similarity	NPD2095	Phase 2
0.7446	Intermediate Similarity	NPD2094	Phase 2
0.7442	Intermediate Similarity	NPD2882	Phase 1
0.7411	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD4601	Approved
0.7409	Intermediate Similarity	NPD4600	Approved
0.7405	Intermediate Similarity	NPD2091	Phase 2
0.7405	Intermediate Similarity	NPD2096	Phase 2
0.7391	Intermediate Similarity	NPD3038	Discontinued
0.7385	Intermediate Similarity	NPD2920	Discontinued
0.7374	Intermediate Similarity	NPD4640	Approved
0.7374	Intermediate Similarity	NPD4639	Approved
0.7374	Intermediate Similarity	NPD4638	Approved
0.7366	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5902	Approved
0.7363	Intermediate Similarity	NPD5903	Approved
0.7363	Intermediate Similarity	NPD5100	Phase 3
0.7358	Intermediate Similarity	NPD2176	Approved
0.7358	Intermediate Similarity	NPD2177	Approved
0.7358	Intermediate Similarity	NPD2175	Phase 3
0.7347	Intermediate Similarity	NPD5901	Discontinued
0.7345	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3525	Discontinued
0.733	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5612	Discontinued
0.7322	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6492	Phase 2
0.7308	Intermediate Similarity	NPD482	Approved
0.7292	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4511	Phase 1
0.7278	Intermediate Similarity	NPD5021	Discontinued
0.7277	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD1038	Approved
0.7273	Intermediate Similarity	NPD1392	Approved
0.7268	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4702	Approved
0.7267	Intermediate Similarity	NPD4703	Approved
0.7258	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD5897	Approved
0.7243	Intermediate Similarity	NPD5898	Approved
0.7243	Intermediate Similarity	NPD6452	Discontinued
0.7243	Intermediate Similarity	NPD5899	Approved
0.7232	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6159	Phase 2
0.7225	Intermediate Similarity	NPD3100	Discontinued
0.7222	Intermediate Similarity	NPD7957	Phase 1
0.7222	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5939	Approved
0.7214	Intermediate Similarity	NPD5936	Approved
0.7206	Intermediate Similarity	NPD5164	Discontinued
0.7196	Intermediate Similarity	NPD4948	Discontinued
0.7193	Intermediate Similarity	NPD5254	Discontinued
0.7188	Intermediate Similarity	NPD802	Phase 2
0.7179	Intermediate Similarity	NPD3814	Phase 1
0.7179	Intermediate Similarity	NPD6248	Phase 2
0.7179	Intermediate Similarity	NPD6249	Phase 2
0.7173	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7418	Discontinued
0.7158	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4602	Approved
0.7143	Intermediate Similarity	NPD6978	Phase 2
0.7143	Intermediate Similarity	NPD7474	Suspended
0.7143	Intermediate Similarity	NPD484	Approved
0.7143	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6455	Phase 3
0.7136	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5255	Approved
0.7129	Intermediate Similarity	NPD7470	Discontinued
0.7128	Intermediate Similarity	NPD7778	Approved
0.7128	Intermediate Similarity	NPD7777	Approved
0.7128	Intermediate Similarity	NPD53	Approved
0.7118	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4204	Approved
0.7112	Intermediate Similarity	NPD4203	Approved
0.7104	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6985	Discontinued
0.7086	Intermediate Similarity	NPD3835	Phase 3
0.7086	Intermediate Similarity	NPD2172	Phase 1
0.7086	Intermediate Similarity	NPD3833	Phase 3
0.7081	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8073	Approved
0.7065	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD750	Phase 2
0.7062	Intermediate Similarity	NPD7944	Discontinued
0.7062	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD786	Approved
0.7056	Intermediate Similarity	NPD4500	Approved
0.7056	Intermediate Similarity	NPD4501	Approved
0.7053	Intermediate Similarity	NPD7194	Discontinued
0.7048	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3404	Approved
0.7044	Intermediate Similarity	NPD5066	Phase 2
0.7044	Intermediate Similarity	NPD5067	Phase 2
0.7041	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8072	Approved
0.7015	Intermediate Similarity	NPD8322	Phase 2
0.7012	Intermediate Similarity	NPD995	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3330	Phase 1
0.7005	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8395	Approved
0.7005	Intermediate Similarity	NPD8396	Approved
0.7	Intermediate Similarity	NPD5426	Phase 3
0.7	Intermediate Similarity	NPD6227	Discontinued
0.7	Intermediate Similarity	NPD8272	Phase 2
0.6995	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5658	Approved
0.6979	Remote Similarity	NPD4334	Discontinued
0.6977	Remote Similarity	NPD7558	Phase 2
0.6965	Remote Similarity	NPD7001	Phase 3
0.6961	Remote Similarity	NPD6220	Phase 3
0.6961	Remote Similarity	NPD4502	Phase 2
0.6954	Remote Similarity	NPD7946	Pre-registration
0.6952	Remote Similarity	NPD8123	Approved
0.6952	Remote Similarity	NPD8122	Approved
0.695	Remote Similarity	NPD6176	Phase 1
0.695	Remote Similarity	NPD5487	Phase 1
0.6943	Remote Similarity	NPD5117	Phase 2
0.6942	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7935	Phase 2
0.6935	Remote Similarity	NPD4128	Approved
0.6932	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6290	Phase 2
0.6931	Remote Similarity	NPD7452	Approved
0.6931	Remote Similarity	NPD7222	Phase 2
0.6931	Remote Similarity	NPD7453	Approved
0.6927	Remote Similarity	NPD8093	Discontinued
0.6923	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6206	Phase 1
0.6898	Remote Similarity	NPD5104	Approved
0.6897	Remote Similarity	NPD2916	Discontinued
0.6888	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2915	Discontinued
0.6882	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1722	Approved
0.6875	Remote Similarity	NPD5256	Discontinued
0.6869	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6261	Phase 3
0.6868	Remote Similarity	NPD1684	Approved
0.6868	Remote Similarity	NPD1685	Approved
0.6867	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4886	Phase 2
0.686	Remote Similarity	NPD4897	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