NPASS Compound

Structure

NPC200726 OpenBabel07101718282D 44 49 0 0 1 0 0 0 0 0999 V2000 -2.8384 0.9900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1913 2.6503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4900 -4.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9800 -3.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9746 2.0624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6383 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2435 -2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 -2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1784 3.0210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -3.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2038 2.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5356 1.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2435 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5770 2.1257 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8487 0.4900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9409 -2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9409 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -0.9800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.9400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8487 -4.4100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8487 0.4900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8487 1.4700 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8487 -1.4700 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3948 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8487 -2.4500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7896 -2.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 -5.3900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7896 -0.9800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5461 -1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 2 0 0 0 0 2 21 1 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 7 37 1 0 0 0 0 9 43 1 0 0 0 0 10 11 2 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 29 1 0 0 0 0 15 35 1 0 0 0 0 16 36 1 0 0 0 0 17 37 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 27 1 0 0 0 0 20 30 1 0 0 0 0 20 35 1 0 0 0 0 22 33 1 0 0 0 0 23 21 1 6 0 0 0 23 31 1 0 0 0 0 24 31 1 0 0 0 0 24 38 1 6 0 0 0 25 26 2 0 0 0 0 25 39 1 0 0 0 0 26 43 1 0 0 0 0 27 32 1 0 0 0 0 27 44 1 6 0 0 0 28 34 1 0 0 0 0 28 36 1 1 0 0 0 29 34 1 0 0 0 0 29 40 1 1 0 0 0 30 38 1 6 0 0 0 30 41 1 0 0 0 0 31 35 1 1 0 0 0 32 36 1 1 0 0 0 32 37 1 0 0 0 0 33 42 2 0 0 0 0 33 44 1 0 0 0 0 35 5 1 1 0 0 0 36 6 1 1 0 0 0 37 38 1 6 0 0 0 38 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.41
Volume:	654.024
LogP:	6.709
LogD:	5.544
LogS:	-4.317
# Rotatable Bonds:	5
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	5.178
Fsp3:	0.763
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.185
MDCK Permeability:	2.6961537514580414e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.707

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	97.18675994873047%
Volume Distribution (VD):	0.941
Pgp-substrate:	7.114927291870117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.663
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.24
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.837
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.511

ADMET: Excretion

Clearance (CL):	8.238
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.817
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.508
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.47
Carcinogencity:	0.005
Eye Corrosion:	0.015
Eye Irritation:	0.106
Respiratory Toxicity:	0.819

Download Data

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

Natural Product: NPC200726

Natural Product ID:	NPC200726
*Common Name:**	Ulmicin A
IUPAC Name:	[(1R,3aR,5S,5aR,5bR,7aR,9S,11aS,11bR,12R,13aR,13bR)-5,9-dihydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-12-yl] 4-hydroxy-3-methoxybenzoate
Synonyms:
Standard InCHIKey:	SFWXTEAVJISKCL-SXURMERUSA-N
Standard InCHI:	InChI=1S/C38H56O6/c1-21(2)23-12-15-35(5)20-30(41)38(8)24(31(23)35)19-27(44-33(42)22-10-11-25(39)26(18-22)43-9)32-36(6)16-14-29(40)34(3,4)28(36)13-17-37(32,38)7/h10-11,18,23-24,27-32,39-41H,1,12-17,19-20H2,2-9H3/t23-,24+,27+,28-,29-,30-,31+,32+,35+,36-,37+,38-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)C[C@@H]([C@]3(C)[C@H](C[C@H]([C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)OC(=O)c3ccc(c(c3)OC)O)[C@@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499750
PubChem CID:	21590542
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO2200.1	Ulmus davidiana	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277749]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	48.0	%	PMID[517654]

☑ 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 NPC200726 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	384
0.1-0.2	1403
0.2-0.3	2897
0.3-0.4	5246
0.4-0.5	9337
0.5-0.6	9021
0.6-0.7	8750
0.7-0.8	5310
0.8-0.85	246
0.85-0.9	86
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC177362
0.9873	High Similarity	NPC202428
0.9873	High Similarity	NPC266545
0.9325	High Similarity	NPC472803
0.9295	High Similarity	NPC205392
0.9295	High Similarity	NPC105942
0.9114	High Similarity	NPC62051
0.9045	High Similarity	NPC118033
0.9038	High Similarity	NPC279442
0.8987	High Similarity	NPC124842
0.8987	High Similarity	NPC475579
0.8987	High Similarity	NPC473773
0.8924	High Similarity	NPC473680
0.8924	High Similarity	NPC475311
0.8924	High Similarity	NPC473579
0.8924	High Similarity	NPC475454
0.8902	High Similarity	NPC100420
0.8896	High Similarity	NPC266365
0.8861	High Similarity	NPC470619
0.8861	High Similarity	NPC208785
0.8861	High Similarity	NPC145527
0.8861	High Similarity	NPC470618
0.8846	High Similarity	NPC8102
0.8846	High Similarity	NPC66894
0.8797	High Similarity	NPC298647
0.8797	High Similarity	NPC273358
0.8782	High Similarity	NPC235195
0.8782	High Similarity	NPC469683
0.8782	High Similarity	NPC19862
0.8779	High Similarity	NPC473205
0.8779	High Similarity	NPC473776
0.8742	High Similarity	NPC142654
0.8742	High Similarity	NPC327962
0.8734	High Similarity	NPC32017
0.8734	High Similarity	NPC96930
0.8718	High Similarity	NPC469615
0.8679	High Similarity	NPC292206
0.8675	High Similarity	NPC45943
0.8662	High Similarity	NPC271607
0.8662	High Similarity	NPC280717
0.8662	High Similarity	NPC307205
0.8654	High Similarity	NPC252133
0.8644	High Similarity	NPC475299
0.8634	High Similarity	NPC267091
0.8616	High Similarity	NPC477483
0.8616	High Similarity	NPC325032
0.8608	High Similarity	NPC75295
0.859	High Similarity	NPC35212
0.8589	High Similarity	NPC472807
0.8588	High Similarity	NPC469775
0.8588	High Similarity	NPC469776
0.8588	High Similarity	NPC469778
0.8588	High Similarity	NPC295941
0.8588	High Similarity	NPC469777
0.8588	High Similarity	NPC469774
0.8588	High Similarity	NPC469773
0.8588	High Similarity	NPC469772
0.8588	High Similarity	NPC100925
0.8588	High Similarity	NPC32723
0.8588	High Similarity	NPC135334
0.858	High Similarity	NPC21956
0.8571	High Similarity	NPC299855
0.8571	High Similarity	NPC96194
0.8571	High Similarity	NPC243891
0.8554	High Similarity	NPC216916
0.8538	High Similarity	NPC316539
0.8535	High Similarity	NPC310621
0.8535	High Similarity	NPC469447
0.8535	High Similarity	NPC477873
0.8529	High Similarity	NPC180768
0.8528	High Similarity	NPC469888
0.8526	High Similarity	NPC473612
0.8523	High Similarity	NPC189704
0.8521	High Similarity	NPC286809
0.8519	High Similarity	NPC48671
0.8509	High Similarity	NPC303989
0.8509	High Similarity	NPC474305
0.8506	High Similarity	NPC188217
0.85	High Similarity	NPC470757
0.8491	Intermediate Similarity	NPC258856
0.8488	Intermediate Similarity	NPC469354
0.8488	Intermediate Similarity	NPC469438
0.8485	Intermediate Similarity	NPC167098
0.8485	Intermediate Similarity	NPC296044
0.8481	Intermediate Similarity	NPC26045
0.8481	Intermediate Similarity	NPC25491
0.8475	Intermediate Similarity	NPC476067
0.8475	Intermediate Similarity	NPC475121
0.8462	Intermediate Similarity	NPC263212
0.8457	Intermediate Similarity	NPC261659
0.8452	Intermediate Similarity	NPC161151
0.8447	Intermediate Similarity	NPC474306
0.8447	Intermediate Similarity	NPC475848
0.8447	Intermediate Similarity	NPC476394
0.8447	Intermediate Similarity	NPC98809
0.8443	Intermediate Similarity	NPC131905
0.8443	Intermediate Similarity	NPC469889
0.8438	Intermediate Similarity	NPC58752
0.843	Intermediate Similarity	NPC98583
0.8428	Intermediate Similarity	NPC53520
0.8418	Intermediate Similarity	NPC235557
0.8408	Intermediate Similarity	NPC27518
0.8408	Intermediate Similarity	NPC304110
0.8397	Intermediate Similarity	NPC234548
0.8397	Intermediate Similarity	NPC248287
0.8393	Intermediate Similarity	NPC145847
0.8393	Intermediate Similarity	NPC476371
0.8393	Intermediate Similarity	NPC476372
0.8389	Intermediate Similarity	NPC476358
0.8385	Intermediate Similarity	NPC472969
0.8383	Intermediate Similarity	NPC24627
0.8383	Intermediate Similarity	NPC185617
0.8383	Intermediate Similarity	NPC476373
0.8373	Intermediate Similarity	NPC143328
0.8372	Intermediate Similarity	NPC100251
0.8372	Intermediate Similarity	NPC65333
0.8365	Intermediate Similarity	NPC473090
0.8364	Intermediate Similarity	NPC300757
0.8364	Intermediate Similarity	NPC180901
0.8354	Intermediate Similarity	NPC131121
0.8344	Intermediate Similarity	NPC119252
0.8343	Intermediate Similarity	NPC108191
0.8343	Intermediate Similarity	NPC109990
0.8343	Intermediate Similarity	NPC100425
0.8343	Intermediate Similarity	NPC93685
0.8343	Intermediate Similarity	NPC277618
0.8333	Intermediate Similarity	NPC478050
0.8333	Intermediate Similarity	NPC475054
0.8333	Intermediate Similarity	NPC469397
0.8324	Intermediate Similarity	NPC230670
0.8324	Intermediate Similarity	NPC71385
0.8324	Intermediate Similarity	NPC475197
0.8324	Intermediate Similarity	NPC473467
0.8324	Intermediate Similarity	NPC195972
0.8323	Intermediate Similarity	NPC179914
0.8323	Intermediate Similarity	NPC246229
0.8323	Intermediate Similarity	NPC474991
0.8323	Intermediate Similarity	NPC191899
0.8313	Intermediate Similarity	NPC470896
0.8313	Intermediate Similarity	NPC7059
0.8313	Intermediate Similarity	NPC471968
0.8313	Intermediate Similarity	NPC473275
0.8303	Intermediate Similarity	NPC305710
0.8302	Intermediate Similarity	NPC176030
0.8302	Intermediate Similarity	NPC141817
0.8302	Intermediate Similarity	NPC229218
0.8302	Intermediate Similarity	NPC169214
0.8302	Intermediate Similarity	NPC192597
0.8294	Intermediate Similarity	NPC310572
0.8293	Intermediate Similarity	NPC121615
0.8293	Intermediate Similarity	NPC294511
0.8291	Intermediate Similarity	NPC470035
0.8291	Intermediate Similarity	NPC172311
0.8284	Intermediate Similarity	NPC473445
0.8284	Intermediate Similarity	NPC476011
0.8282	Intermediate Similarity	NPC261322
0.8282	Intermediate Similarity	NPC237441
0.828	Intermediate Similarity	NPC182249
0.828	Intermediate Similarity	NPC132723
0.828	Intermediate Similarity	NPC76032
0.8278	Intermediate Similarity	NPC112708
0.8274	Intermediate Similarity	NPC21046
0.8274	Intermediate Similarity	NPC79571
0.8274	Intermediate Similarity	NPC53889
0.8272	Intermediate Similarity	NPC127046
0.8266	Intermediate Similarity	NPC148185
0.8263	Intermediate Similarity	NPC187205
0.8263	Intermediate Similarity	NPC268602
0.8263	Intermediate Similarity	NPC226759
0.8256	Intermediate Similarity	NPC216403
0.8256	Intermediate Similarity	NPC186100
0.8256	Intermediate Similarity	NPC41494
0.825	Intermediate Similarity	NPC471876
0.825	Intermediate Similarity	NPC46161
0.825	Intermediate Similarity	NPC239608
0.8246	Intermediate Similarity	NPC43065
0.8246	Intermediate Similarity	NPC296558
0.8242	Intermediate Similarity	NPC295646
0.8242	Intermediate Similarity	NPC180388
0.8242	Intermediate Similarity	NPC178574
0.8242	Intermediate Similarity	NPC65591
0.8235	Intermediate Similarity	NPC272750
0.8235	Intermediate Similarity	NPC134047
0.8235	Intermediate Similarity	NPC223006
0.8235	Intermediate Similarity	NPC173729
0.8235	Intermediate Similarity	NPC291977
0.8232	Intermediate Similarity	NPC473711
0.8232	Intermediate Similarity	NPC140133
0.8229	Intermediate Similarity	NPC67629
0.8229	Intermediate Similarity	NPC79736
0.8229	Intermediate Similarity	NPC472723
0.8228	Intermediate Similarity	NPC473591
0.8228	Intermediate Similarity	NPC470616
0.8228	Intermediate Similarity	NPC155192
0.8228	Intermediate Similarity	NPC470617
0.8228	Intermediate Similarity	NPC271494
0.8221	Intermediate Similarity	NPC253591
0.8214	Intermediate Similarity	NPC470339
0.8214	Intermediate Similarity	NPC87317
0.8214	Intermediate Similarity	NPC8389

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 NPC200726 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	848
0.2-0.3	1720
0.3-0.4	2567
0.4-0.5	2082
0.5-0.6	1127
0.6-0.7	386
0.7-0.8	83
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD8127	Discontinued
0.8354	Intermediate Similarity	NPD8166	Discontinued
0.8343	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD7685	Pre-registration
0.8305	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4628	Phase 3
0.8098	Intermediate Similarity	NPD6273	Approved
0.8095	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7458	Discontinued
0.8046	Intermediate Similarity	NPD5844	Phase 1
0.7989	Intermediate Similarity	NPD7228	Approved
0.7955	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD6234	Discontinued
0.7861	Intermediate Similarity	NPD6232	Discontinued
0.7821	Intermediate Similarity	NPD8312	Approved
0.7821	Intermediate Similarity	NPD8313	Approved
0.7811	Intermediate Similarity	NPD37	Approved
0.7791	Intermediate Similarity	NPD7003	Approved
0.7778	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4965	Approved
0.7771	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1934	Approved
0.7701	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD8434	Phase 2
0.7684	Intermediate Similarity	NPD3818	Discontinued
0.7673	Intermediate Similarity	NPD3620	Phase 2
0.7673	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1465	Phase 2
0.764	Intermediate Similarity	NPD7054	Approved
0.7636	Intermediate Similarity	NPD6190	Approved
0.7598	Intermediate Similarity	NPD7472	Approved
0.7592	Intermediate Similarity	NPD7497	Discontinued
0.7576	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4110	Phase 3
0.7572	Intermediate Similarity	NPD3882	Suspended
0.7558	Intermediate Similarity	NPD2801	Approved
0.7558	Intermediate Similarity	NPD5761	Phase 2
0.7558	Intermediate Similarity	NPD5760	Phase 2
0.7543	Intermediate Similarity	NPD5494	Approved
0.7516	Intermediate Similarity	NPD230	Phase 1
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7240	Approved
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7485	Intermediate Similarity	NPD7236	Approved
0.7485	Intermediate Similarity	NPD7028	Phase 2
0.7473	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7808	Phase 3
0.7468	Intermediate Similarity	NPD9494	Approved
0.7457	Intermediate Similarity	NPD7819	Suspended
0.7429	Intermediate Similarity	NPD7075	Discontinued
0.7418	Intermediate Similarity	NPD7251	Discontinued
0.7414	Intermediate Similarity	NPD3817	Phase 2
0.7412	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2533	Approved
0.7396	Intermediate Similarity	NPD2532	Approved
0.7396	Intermediate Similarity	NPD2534	Approved
0.7394	Intermediate Similarity	NPD5762	Approved
0.7394	Intermediate Similarity	NPD5763	Approved
0.7391	Intermediate Similarity	NPD6663	Approved
0.7391	Intermediate Similarity	NPD8032	Phase 2
0.7371	Intermediate Similarity	NPD7768	Phase 2
0.7363	Intermediate Similarity	NPD6797	Phase 2
0.7358	Intermediate Similarity	NPD5736	Approved
0.7356	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8455	Phase 2
0.7346	Intermediate Similarity	NPD4140	Approved
0.7341	Intermediate Similarity	NPD6385	Approved
0.7341	Intermediate Similarity	NPD6386	Approved
0.7329	Intermediate Similarity	NPD3764	Approved
0.7326	Intermediate Similarity	NPD3226	Approved
0.7326	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6764	Approved
0.7322	Intermediate Similarity	NPD6765	Approved
0.7314	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8151	Discontinued
0.7303	Intermediate Similarity	NPD6959	Discontinued
0.7301	Intermediate Similarity	NPD6355	Discontinued
0.7294	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7266	Discontinued
0.7283	Intermediate Similarity	NPD6599	Discontinued
0.7278	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7239	Suspended
0.7262	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1511	Approved
0.7232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7435	Discontinued
0.7231	Intermediate Similarity	NPD7680	Approved
0.7229	Intermediate Similarity	NPD2935	Discontinued
0.7212	Intermediate Similarity	NPD7097	Phase 1
0.7202	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6801	Discontinued
0.7198	Intermediate Similarity	NPD7799	Discontinued
0.7195	Intermediate Similarity	NPD5735	Approved
0.7166	Intermediate Similarity	NPD6785	Approved
0.7166	Intermediate Similarity	NPD6784	Approved
0.716	Intermediate Similarity	NPD3027	Phase 3
0.716	Intermediate Similarity	NPD3750	Approved
0.7151	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7135	Intermediate Similarity	NPD7038	Approved
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7135	Intermediate Similarity	NPD7039	Approved
0.7119	Intermediate Similarity	NPD5402	Approved
0.7119	Intermediate Similarity	NPD5353	Approved
0.7112	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7870	Phase 2
0.7107	Intermediate Similarity	NPD7871	Phase 2
0.7104	Intermediate Similarity	NPD7177	Discontinued
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.71	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7874	Approved
0.7091	Intermediate Similarity	NPD447	Suspended
0.7083	Intermediate Similarity	NPD2346	Discontinued
0.7077	Intermediate Similarity	NPD6782	Approved
0.7077	Intermediate Similarity	NPD6776	Approved
0.7077	Intermediate Similarity	NPD6777	Approved
0.7077	Intermediate Similarity	NPD6779	Approved
0.7077	Intermediate Similarity	NPD6781	Approved
0.7077	Intermediate Similarity	NPD6778	Approved
0.7077	Intermediate Similarity	NPD6780	Approved
0.7066	Intermediate Similarity	NPD2799	Discontinued
0.7056	Intermediate Similarity	NPD7698	Approved
0.7056	Intermediate Similarity	NPD7697	Approved
0.7056	Intermediate Similarity	NPD7696	Phase 3
0.7055	Intermediate Similarity	NPD7095	Approved
0.7051	Intermediate Similarity	NPD9545	Approved
0.7048	Intermediate Similarity	NPD6653	Approved
0.7045	Intermediate Similarity	NPD6873	Phase 2
0.7044	Intermediate Similarity	NPD1608	Approved
0.7039	Intermediate Similarity	NPD3749	Approved
0.7035	Intermediate Similarity	NPD6799	Approved
0.7033	Intermediate Similarity	NPD5242	Approved
0.703	Intermediate Similarity	NPD4060	Phase 1
0.7024	Intermediate Similarity	NPD6100	Approved
0.7024	Intermediate Similarity	NPD6099	Approved
0.7022	Intermediate Similarity	NPD5977	Approved
0.7022	Intermediate Similarity	NPD5978	Approved
0.702	Intermediate Similarity	NPD8319	Approved
0.702	Intermediate Similarity	NPD8320	Phase 1
0.7016	Intermediate Similarity	NPD2488	Approved
0.7016	Intermediate Similarity	NPD2490	Approved
0.7012	Intermediate Similarity	NPD6798	Discontinued
0.7011	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD7701	Phase 2
0.6994	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6002	Phase 3
0.6982	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6004	Phase 3
0.6982	Remote Similarity	NPD6005	Phase 3
0.698	Remote Similarity	NPD7801	Approved
0.698	Remote Similarity	NPD7783	Phase 2
0.698	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3787	Discontinued
0.6978	Remote Similarity	NPD7229	Phase 3
0.6971	Remote Similarity	NPD1653	Approved
0.6968	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1510	Phase 2
0.6964	Remote Similarity	NPD7033	Discontinued
0.6962	Remote Similarity	NPD3019	Approved
0.6957	Remote Similarity	NPD1283	Approved
0.6957	Remote Similarity	NPD1876	Approved
0.6954	Remote Similarity	NPD2493	Approved
0.6954	Remote Similarity	NPD2494	Approved
0.6951	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6677	Suspended
0.6944	Remote Similarity	NPD7831	Phase 2
0.6944	Remote Similarity	NPD7833	Phase 2
0.6944	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1549	Phase 2
0.6938	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3972	Approved
0.6935	Remote Similarity	NPD4583	Approved
0.6935	Remote Similarity	NPD4582	Approved
0.6933	Remote Similarity	NPD2861	Phase 2
0.6932	Remote Similarity	NPD3455	Phase 2
0.6928	Remote Similarity	NPD2979	Phase 3
0.6928	Remote Similarity	NPD1613	Approved
0.6928	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5408	Approved
0.6923	Remote Similarity	NPD2438	Suspended
0.6923	Remote Similarity	NPD5404	Approved
0.6923	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD5405	Approved
0.6919	Remote Similarity	NPD2491	Approved
0.6919	Remote Similarity	NPD3057	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