NPASS Compound

Structure

CID160105 OpenBabel06191715532D 35 37 0 0 1 0 0 0 0 0999 V2000 -3.3142 0.7916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9528 -0.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4969 4.6797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8669 -1.4997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6471 0.9567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1470 1.8225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6473 0.9567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6471 2.6883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4265 1.3614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0650 3.0247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6681 3.0609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6446 0.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9089 3.8705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8665 -0.4995 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1695 2.0304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1474 1.8225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6473 2.6883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4757 1.6703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0749 2.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6941 0.3589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0860 3.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7327 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2675 2.6482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9507 -0.3095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9784 3.4313 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6739 3.1659 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3157 2.9574 0.0000 N 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 1.7321 1.0012 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4868 1.3387 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0694 2.0431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4927 4.8890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5989 -0.4991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0105 3.3175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1580 -1.2878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 2 0 0 0 0 9 15 1 0 0 0 0 10 15 2 0 0 0 0 10 25 1 0 0 0 0 11 19 1 0 0 0 0 11 26 1 0 0 0 0 13 3 1 6 0 0 0 13 21 1 0 0 0 0 13 27 1 0 0 0 0 14 4 1 6 0 0 0 14 22 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 25 1 0 0 0 0 18 9 1 6 0 0 0 18 23 1 0 0 0 0 18 29 1 0 0 0 0 19 30 2 3 0 0 0 19 31 1 0 0 0 0 20 12 1 6 0 0 0 20 24 1 0 0 0 0 20 30 1 0 0 0 0 21 26 2 3 0 0 0 21 32 1 0 0 0 0 22 29 2 3 0 0 0 22 33 1 0 0 0 0 23 27 2 3 0 0 0 23 34 1 0 0 0 0 24 28 2 3 0 0 0 24 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.24
Volume:	484.194
LogP:	0.538
LogD:	1.17
LogS:	-3.246
# Rotatable Bonds:	3
TPSA:	161.29
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.345
Synthetic Accessibility Score:	4.421
Fsp3:	0.458
Lipinski Rule-of-5:	Rejected
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:	-6.34
MDCK Permeability:	5.741615950682899e-06
Pgp-inhibitor:	0.201
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.259
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.306
Plasma Protein Binding (PPB):	40.475074768066406%
Volume Distribution (VD):	0.445
Pgp-substrate:	58.27246856689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.25
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	4.398
Half-life (T1/2):	0.813

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.358
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.195
Skin Sensitization:	0.265
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC160105

Natural Product ID:	NPC160105
*Common Name:**	Segetalin B
IUPAC Name:	(3S,6S,9S,12S)-6-(1H-indol-3-ylmethyl)-3,9-dimethyl-12-propan-2-yl-1,4,7,10,13-pentazacyclopentadecane-2,5,8,11,14-pentone
Synonyms:
Standard InCHIKey:	VBQDUSUKSGAFMN-OACKDKIBSA-N
Standard InCHI:	InChI=1S/C24H32N6O5/c1-12(2)20-24(35)28-14(4)22(33)29-18(9-15-10-25-17-8-6-5-7-16(15)17)23(34)27-13(3)21(32)26-11-19(31)30-20/h5-8,10,12-14,18,20,25H,9,11H2,1-4H3,(H,26,32)(H,27,34)(H,28,35)(H,29,33)(H,30,31)/t13-,14-,18-,20-/m0/s1
SMILES:	CC(C)[C@H]1C(=N[C@@H](C)C(=N[C@@H](Cc2c[nH]c3ccccc23)C(=N[C@@H](C)C(=NCC(=N1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL386632
PubChem CID:	10345235
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:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO40525	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[9157189]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6752	Melandryum firmum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	56.3	mg	PMID[450211]

☑ 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 NPC160105 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	366
0.1-0.2	2989
0.2-0.3	18939
0.3-0.4	12900
0.4-0.5	3070
0.5-0.6	2287
0.6-0.7	1348
0.7-0.8	594
0.8-0.85	120
0.85-0.9	52
0.9-0.95	27
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC314603
0.961	High Similarity	NPC474561
0.961	High Similarity	NPC49954
0.9416	High Similarity	NPC282231
0.9404	High Similarity	NPC469760
0.9404	High Similarity	NPC73952
0.9404	High Similarity	NPC469763
0.9404	High Similarity	NPC469765
0.9404	High Similarity	NPC469786
0.9404	High Similarity	NPC25008
0.9404	High Similarity	NPC259644
0.9351	High Similarity	NPC279918
0.9342	High Similarity	NPC80597
0.9342	High Similarity	NPC211572
0.9342	High Similarity	NPC70922
0.9342	High Similarity	NPC212376
0.9342	High Similarity	NPC75540
0.9299	High Similarity	NPC63751
0.9231	High Similarity	NPC194640
0.9221	High Similarity	NPC469762
0.9156	High Similarity	NPC469785
0.9114	High Similarity	NPC54988
0.9108	High Similarity	NPC311276
0.9074	High Similarity	NPC59269
0.9042	High Similarity	NPC213629
0.9024	High Similarity	NPC233936
0.9007	High Similarity	NPC314372
0.8957	High Similarity	NPC248454
0.8938	High Similarity	NPC201700
0.8896	High Similarity	NPC24678
0.8896	High Similarity	NPC105818
0.8896	High Similarity	NPC267885
0.8874	High Similarity	NPC190296
0.8868	High Similarity	NPC40779
0.8834	High Similarity	NPC203468
0.8834	High Similarity	NPC149155
0.8834	High Similarity	NPC110500
0.881	High Similarity	NPC474707
0.881	High Similarity	NPC235684
0.8797	High Similarity	NPC230869
0.879	High Similarity	NPC285469
0.8788	High Similarity	NPC248041
0.8788	High Similarity	NPC283219
0.8788	High Similarity	NPC126709
0.8757	High Similarity	NPC317030
0.8743	High Similarity	NPC163055
0.8742	High Similarity	NPC469767
0.8742	High Similarity	NPC469768
0.8742	High Similarity	NPC469761
0.8742	High Similarity	NPC469784
0.8742	High Similarity	NPC469783
0.8742	High Similarity	NPC469779
0.8742	High Similarity	NPC469780
0.8706	High Similarity	NPC65215
0.8706	High Similarity	NPC173028
0.8704	High Similarity	NPC78020
0.8698	High Similarity	NPC94752
0.8684	High Similarity	NPC469766
0.8647	High Similarity	NPC204565
0.8636	High Similarity	NPC159856
0.8629	High Similarity	NPC473640
0.8629	High Similarity	NPC171317
0.8625	High Similarity	NPC131718
0.8614	High Similarity	NPC14113
0.8614	High Similarity	NPC145885
0.8614	High Similarity	NPC84827
0.8596	High Similarity	NPC321708
0.858	High Similarity	NPC100321
0.858	High Similarity	NPC293917
0.8571	High Similarity	NPC16667
0.8563	High Similarity	NPC213468
0.8553	High Similarity	NPC73767
0.8543	High Similarity	NPC84911
0.8529	High Similarity	NPC15102
0.8526	High Similarity	NPC471957
0.8512	High Similarity	NPC300688
0.8506	High Similarity	NPC474177
0.8503	High Similarity	NPC151939
0.8491	Intermediate Similarity	NPC207726
0.8483	Intermediate Similarity	NPC475506
0.8477	Intermediate Similarity	NPC261195
0.8477	Intermediate Similarity	NPC29886
0.8477	Intermediate Similarity	NPC96102
0.8471	Intermediate Similarity	NPC165495
0.8457	Intermediate Similarity	NPC133366
0.8448	Intermediate Similarity	NPC477167
0.8448	Intermediate Similarity	NPC473342
0.8447	Intermediate Similarity	NPC67056
0.8439	Intermediate Similarity	NPC95783
0.8436	Intermediate Similarity	NPC155143
0.8431	Intermediate Similarity	NPC110126
0.8424	Intermediate Similarity	NPC194411
0.8424	Intermediate Similarity	NPC280548
0.8421	Intermediate Similarity	NPC163421
0.8421	Intermediate Similarity	NPC105127
0.8421	Intermediate Similarity	NPC188387
0.8405	Intermediate Similarity	NPC102423
0.8393	Intermediate Similarity	NPC68354
0.8363	Intermediate Similarity	NPC228835
0.8343	Intermediate Similarity	NPC55772
0.8343	Intermediate Similarity	NPC473376
0.8333	Intermediate Similarity	NPC92796
0.8333	Intermediate Similarity	NPC135141
0.8333	Intermediate Similarity	NPC193761
0.8333	Intermediate Similarity	NPC476874
0.8323	Intermediate Similarity	NPC313791
0.8314	Intermediate Similarity	NPC280290
0.8314	Intermediate Similarity	NPC314002
0.8302	Intermediate Similarity	NPC53947
0.8284	Intermediate Similarity	NPC111275
0.8274	Intermediate Similarity	NPC37423
0.8274	Intermediate Similarity	NPC275305
0.8272	Intermediate Similarity	NPC129721
0.8266	Intermediate Similarity	NPC171171
0.8263	Intermediate Similarity	NPC470498
0.8258	Intermediate Similarity	NPC229332
0.8258	Intermediate Similarity	NPC279081
0.8256	Intermediate Similarity	NPC204717
0.825	Intermediate Similarity	NPC216713
0.8246	Intermediate Similarity	NPC71037
0.8242	Intermediate Similarity	NPC470508
0.8239	Intermediate Similarity	NPC37548
0.8218	Intermediate Similarity	NPC17059
0.8214	Intermediate Similarity	NPC472123
0.8212	Intermediate Similarity	NPC470499
0.8212	Intermediate Similarity	NPC82295
0.8207	Intermediate Similarity	NPC314957
0.8202	Intermediate Similarity	NPC11445
0.8199	Intermediate Similarity	NPC200214
0.8198	Intermediate Similarity	NPC220765
0.8193	Intermediate Similarity	NPC49217
0.8166	Intermediate Similarity	NPC469938
0.8162	Intermediate Similarity	NPC107077
0.8162	Intermediate Similarity	NPC223791
0.8156	Intermediate Similarity	NPC262898
0.8152	Intermediate Similarity	NPC54420
0.8152	Intermediate Similarity	NPC323927
0.8146	Intermediate Similarity	NPC195239
0.8146	Intermediate Similarity	NPC157828
0.8144	Intermediate Similarity	NPC317430
0.8141	Intermediate Similarity	NPC230002
0.8136	Intermediate Similarity	NPC304187
0.8136	Intermediate Similarity	NPC477166
0.8136	Intermediate Similarity	NPC99666
0.8129	Intermediate Similarity	NPC176199
0.8129	Intermediate Similarity	NPC215795
0.8129	Intermediate Similarity	NPC11126
0.8122	Intermediate Similarity	NPC470497
0.8114	Intermediate Similarity	NPC46580
0.8113	Intermediate Similarity	NPC143872
0.8113	Intermediate Similarity	NPC288838
0.811	Intermediate Similarity	NPC206819
0.811	Intermediate Similarity	NPC318065
0.811	Intermediate Similarity	NPC56765
0.811	Intermediate Similarity	NPC41257
0.8101	Intermediate Similarity	NPC179701
0.8092	Intermediate Similarity	NPC469358
0.8084	Intermediate Similarity	NPC109447
0.8079	Intermediate Similarity	NPC117244
0.8079	Intermediate Similarity	NPC243716
0.8079	Intermediate Similarity	NPC473763
0.8075	Intermediate Similarity	NPC320968
0.8065	Intermediate Similarity	NPC478158
0.8065	Intermediate Similarity	NPC162860
0.8059	Intermediate Similarity	NPC472586
0.8059	Intermediate Similarity	NPC329688
0.8059	Intermediate Similarity	NPC189812
0.8057	Intermediate Similarity	NPC315555
0.8056	Intermediate Similarity	NPC227582
0.8049	Intermediate Similarity	NPC286427
0.8037	Intermediate Similarity	NPC38736
0.8037	Intermediate Similarity	NPC470507
0.8032	Intermediate Similarity	NPC75726
0.8032	Intermediate Similarity	NPC31385
0.8032	Intermediate Similarity	NPC110602
0.8032	Intermediate Similarity	NPC75634
0.8023	Intermediate Similarity	NPC219336
0.8012	Intermediate Similarity	NPC321911
0.8012	Intermediate Similarity	NPC187951
0.8011	Intermediate Similarity	NPC265576
0.8	Intermediate Similarity	NPC34508
0.7989	Intermediate Similarity	NPC48938
0.7989	Intermediate Similarity	NPC472108
0.7989	Intermediate Similarity	NPC54744
0.7989	Intermediate Similarity	NPC307963
0.7989	Intermediate Similarity	NPC139291
0.7988	Intermediate Similarity	NPC141353
0.7987	Intermediate Similarity	NPC242556
0.7965	Intermediate Similarity	NPC15573
0.7965	Intermediate Similarity	NPC183662
0.7965	Intermediate Similarity	NPC217372
0.7965	Intermediate Similarity	NPC184964
0.7956	Intermediate Similarity	NPC156704
0.7955	Intermediate Similarity	NPC62749
0.795	Intermediate Similarity	NPC469811
0.795	Intermediate Similarity	NPC179787
0.795	Intermediate Similarity	NPC201380
0.7943	Intermediate Similarity	NPC472294
0.7939	Intermediate Similarity	NPC216643
0.7923	Intermediate Similarity	NPC252338

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 NPC160105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	518
0.2-0.3	1044
0.3-0.4	1445
0.4-0.5	2678
0.5-0.6	2133
0.6-0.7	899
0.7-0.8	203
0.8-0.85	24
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.974	High Similarity	NPD4184	Clinical (unspecified phase)
0.908	High Similarity	NPD6595	Phase 3
0.9042	High Similarity	NPD8110	Clinical (unspecified phase)
0.8982	High Similarity	NPD8431	Approved
0.897	High Similarity	NPD5728	Clinical (unspecified phase)
0.8855	High Similarity	NPD2092	Phase 2
0.8855	High Similarity	NPD2095	Phase 2
0.8855	High Similarity	NPD2094	Phase 2
0.8834	High Similarity	NPD482	Approved
0.8802	High Similarity	NPD2096	Phase 2
0.8802	High Similarity	NPD2091	Phase 2
0.878	High Similarity	NPD749	Clinical (unspecified phase)
0.875	High Similarity	NPD6610	Clinical (unspecified phase)
0.8675	High Similarity	NPD786	Approved
0.8614	High Similarity	NPD2144	Approved
0.858	High Similarity	NPD7621	Clinical (unspecified phase)
0.8571	High Similarity	NPD3038	Discontinued
0.8545	High Similarity	NPD750	Phase 2
0.8503	High Similarity	NPD6203	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD5065	Approved
0.8477	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7948	Phase 1
0.8452	Intermediate Similarity	NPD4076	Approved
0.8452	Intermediate Similarity	NPD4079	Approved
0.8442	Intermediate Similarity	NPD1722	Approved
0.8402	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD3505	Approved
0.8393	Intermediate Similarity	NPD3506	Approved
0.8389	Intermediate Similarity	NPD8072	Approved
0.8343	Intermediate Similarity	NPD8272	Phase 2
0.8333	Intermediate Similarity	NPD8073	Approved
0.8297	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.8297	Intermediate Similarity	NPD7957	Phase 1
0.8253	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8251	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD3100	Discontinued
0.8235	Intermediate Similarity	NPD8386	Phase 2
0.8225	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD1325	Approved
0.8204	Intermediate Similarity	NPD1326	Approved
0.8187	Intermediate Similarity	NPD2172	Phase 1
0.8075	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD4462	Approved
0.8075	Intermediate Similarity	NPD7470	Discontinued
0.8075	Intermediate Similarity	NPD4463	Approved
0.807	Intermediate Similarity	NPD4181	Approved
0.8059	Intermediate Similarity	NPD4128	Approved
0.8021	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8026	Phase 1
0.8011	Intermediate Similarity	NPD3961	Discontinued
0.8011	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD1038	Approved
0.7989	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3323	Discontinued
0.7952	Intermediate Similarity	NPD1404	Approved
0.7952	Intermediate Similarity	NPD1403	Approved
0.795	Intermediate Similarity	NPD4702	Approved
0.795	Intermediate Similarity	NPD4703	Approved
0.7947	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4640	Approved
0.7929	Intermediate Similarity	NPD4639	Approved
0.7929	Intermediate Similarity	NPD2641	Approved
0.7929	Intermediate Similarity	NPD2640	Approved
0.7929	Intermediate Similarity	NPD4638	Approved
0.7929	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4075	Phase 2
0.7901	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD802	Phase 2
0.787	Intermediate Similarity	NPD2639	Approved
0.787	Intermediate Similarity	NPD2642	Approved
0.7866	Intermediate Similarity	NPD2837	Discontinued
0.7845	Intermediate Similarity	NPD7618	Phase 3
0.7845	Intermediate Similarity	NPD7619	Phase 3
0.7845	Intermediate Similarity	NPD7944	Discontinued
0.7833	Intermediate Similarity	NPD3404	Approved
0.7831	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD484	Approved
0.7824	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD3717	Discontinued
0.7807	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD5426	Phase 3
0.7751	Intermediate Similarity	NPD5138	Approved
0.7751	Intermediate Similarity	NPD5140	Approved
0.775	Intermediate Similarity	NPD1592	Phase 3
0.7733	Intermediate Similarity	NPD3610	Approved
0.7733	Intermediate Similarity	NPD3609	Approved
0.7692	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD6664	Approved
0.766	Intermediate Similarity	NPD5901	Discontinued
0.7629	Intermediate Similarity	NPD5612	Discontinued
0.76	Intermediate Similarity	NPD5100	Phase 3
0.7594	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7271	Approved
0.7579	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7970	Approved
0.7571	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD8093	Discontinued
0.7557	Intermediate Similarity	NPD8123	Approved
0.7557	Intermediate Similarity	NPD8122	Approved
0.7556	Intermediate Similarity	NPD6217	Discontinued
0.755	Intermediate Similarity	NPD7711	Discontinued
0.7546	Intermediate Similarity	NPD5254	Discontinued
0.7542	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8094	Discontinued
0.7515	Intermediate Similarity	NPD1661	Suspended
0.7514	Intermediate Similarity	NPD5021	Discontinued
0.7514	Intermediate Similarity	NPD2844	Phase 3
0.7514	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7730	Approved
0.7512	Intermediate Similarity	NPD7731	Approved
0.75	Intermediate Similarity	NPD3654	Approved
0.7486	Intermediate Similarity	NPD5105	Approved
0.7486	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5106	Approved
0.7485	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2119	Approved
0.7484	Intermediate Similarity	NPD991	Phase 2
0.7484	Intermediate Similarity	NPD2118	Approved
0.7471	Intermediate Similarity	NPD5255	Approved
0.7459	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2580	Discontinued
0.7456	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3475	Approved
0.7452	Intermediate Similarity	NPD3476	Approved
0.7446	Intermediate Similarity	NPD4615	Phase 2
0.7442	Intermediate Similarity	NPD8129	Discovery
0.744	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7824	Approved
0.7432	Intermediate Similarity	NPD5117	Phase 2
0.7432	Intermediate Similarity	NPD4499	Approved
0.7429	Intermediate Similarity	NPD3116	Approved
0.7429	Intermediate Similarity	NPD3117	Approved
0.7418	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4547	Phase 3
0.7409	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1392	Approved
0.7391	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5596	Phase 2
0.7381	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6158	Phase 2
0.7378	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2006	Phase 2
0.7368	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2430	Phase 2
0.7363	Intermediate Similarity	NPD706	Phase 1
0.736	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2189	Approved
0.7358	Intermediate Similarity	NPD2187	Approved
0.7354	Intermediate Similarity	NPD4601	Approved
0.7354	Intermediate Similarity	NPD4600	Approved
0.7354	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1683	Approved
0.7349	Intermediate Similarity	NPD7469	Discontinued
0.7348	Intermediate Similarity	NPD6178	Phase 3
0.7345	Intermediate Similarity	NPD2928	Phase 2
0.7337	Intermediate Similarity	NPD6281	Approved
0.7333	Intermediate Similarity	NPD3178	Discontinued
0.7333	Intermediate Similarity	NPD8408	Discontinued
0.7333	Intermediate Similarity	NPD3813	Approved
0.733	Intermediate Similarity	NPD7951	Approved
0.733	Intermediate Similarity	NPD7791	Approved
0.733	Intermediate Similarity	NPD7952	Approved
0.733	Intermediate Similarity	NPD7953	Approved
0.733	Intermediate Similarity	NPD7789	Approved
0.733	Intermediate Similarity	NPD7950	Approved
0.733	Intermediate Similarity	NPD7790	Approved
0.7323	Intermediate Similarity	NPD5818	Discontinued
0.7323	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5862	Discovery
0.7312	Intermediate Similarity	NPD4029	Approved
0.7312	Intermediate Similarity	NPD4030	Approved
0.7312	Intermediate Similarity	NPD4028	Approved
0.7312	Intermediate Similarity	NPD3385	Approved
0.7306	Intermediate Similarity	NPD8322	Phase 2
0.7303	Intermediate Similarity	NPD2380	Approved
0.7303	Intermediate Similarity	NPD2381	Approved
0.7303	Intermediate Similarity	NPD2382	Approved
0.7302	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6999	Discontinued
0.7296	Intermediate Similarity	NPD3330	Phase 1

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