Structure

Physi-Chem Properties

Molecular Weight:  302.22
Volume:  350.318
LogP:  4.263
LogD:  3.8
LogS:  -4.665
# Rotatable Bonds:  2
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.652
Synthetic Accessibility Score:  3.635
Fsp3:  0.55
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.003
MDCK Permeability:  2.9998820537002757e-05
Pgp-inhibitor:  0.073
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.031
Plasma Protein Binding (PPB):  95.98831939697266%
Volume Distribution (VD):  0.457
Pgp-substrate:  1.4550848007202148%

ADMET: Metabolism

CYP1A2-inhibitor:  0.27
CYP1A2-substrate:  0.814
CYP2C19-inhibitor:  0.055
CYP2C19-substrate:  0.446
CYP2C9-inhibitor:  0.42
CYP2C9-substrate:  0.948
CYP2D6-inhibitor:  0.54
CYP2D6-substrate:  0.874
CYP3A4-inhibitor:  0.042
CYP3A4-substrate:  0.191

ADMET: Excretion

Clearance (CL):  1.073
Half-life (T1/2):  0.642

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.674
Drug-inuced Liver Injury (DILI):  0.03
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.017
Maximum Recommended Daily Dose:  0.803
Skin Sensitization:  0.946
Carcinogencity:  0.061
Eye Corrosion:  0.005
Eye Irritation:  0.096
Respiratory Toxicity:  0.769

Download Data

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

  Natural Product: NPC142423

Natural Product ID:  NPC142423
Common Name*:   Crotocembraneic Acid
IUPAC Name:   (1Z,5E,9E,11E)-5,9-dimethyl-12-propan-2-ylcyclotetradeca-1,5,9,11-tetraene-1-carboxylic acid
Synonyms:   Crotocembraneic Acid
Standard InCHIKey:  PJVZQWKLUCVIQA-RJVZQQKXSA-N
Standard InCHI:  InChI=1S/C20H30O2/c1-15(2)18-12-11-17(4)8-5-7-16(3)9-6-10-19(14-13-18)20(21)22/h7,10-12,15H,5-6,8-9,13-14H2,1-4H3,(H,21,22)/b16-7+,17-11+,18-12+,19-10-
SMILES:  CC(C)/C/1=C/C=C(C)/CC/C=C(C)/CC/C=C(/CC1)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL505258
PubChem CID:   5471235
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0000008] Cembrane diterpenoids

*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
NPO16932 Croton oblongifolius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[10479328]
NPO16932 Croton oblongifolius Species Euphorbiaceae Eukaryota stem bark n.a. n.a. PMID[17341114]
NPO16932 Croton oblongifolius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16932 Croton oblongifolius Species Euphorbiaceae 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 45289.76 nM PMID[495867]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 59020.11 nM PMID[495867]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 34514.37 nM PMID[495867]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 36475.39 nM PMID[495867]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 72777.98 nM PMID[495867]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 92257.14 nM PMID[495867]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 33036.95 nM PMID[495867]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 37931.5 nM PMID[495867]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 61235.04 nM PMID[495867]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 35974.93 nM PMID[495867]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 70145.53 nM PMID[495867]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 20989.4 nM PMID[495867]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 33884.42 nM PMID[495867]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 28313.92 nM PMID[495867]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 22855.99 nM PMID[495867]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 29580.12 nM PMID[495867]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 44771.33 nM PMID[495867]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 35075.19 nM PMID[495867]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 66221.65 nM PMID[495867]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[495867]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 53333.49 nM PMID[495867]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 56493.7 nM PMID[495867]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 56754.46 nM PMID[495867]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 22029.26 nM PMID[495867]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 42266.86 nM PMID[495867]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 38106.58 nM PMID[495867]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 42854.85 nM PMID[495867]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 44977.99 nM PMID[495867]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 53088.44 nM PMID[495867]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 22803.42 nM PMID[495867]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 55080.77 nM PMID[495867]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 54827.7 nM PMID[495867]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 61517.69 nM PMID[495867]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 25703.96 nM PMID[495867]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 34276.78 nM PMID[495867]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 77268.06 nM PMID[495867]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 37583.74 nM PMID[495867]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 40271.7 nM PMID[495867]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 37844.26 nM PMID[495867]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 72777.98 nM PMID[495867]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 38994.2 nM PMID[495867]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 34197.94 nM PMID[495867]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 40179.08 nM PMID[495867]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 23227.37 nM PMID[495867]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 35481.34 nM PMID[495867]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 34753.62 nM PMID[495867]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 25763.21 nM PMID[495867]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 44360.86 nM PMID[495867]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 49888.45 nM PMID[495867]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 26730.06 nM PMID[495867]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 61094.2 nM PMID[495867]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 72110.75 nM PMID[495867]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 82794.22 nM PMID[495867]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 55718.57 nM PMID[495867]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 30478.95 nM PMID[495867]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 33036.95 nM PMID[495867]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 46665.94 nM PMID[495867]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[495867]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 19906.73 nM PMID[495867]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 29376.5 nM PMID[495867]

☑ 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 NPC142423 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC308294
0.8676 High Similarity NPC288667
0.8485 Intermediate Similarity NPC322035
0.8485 Intermediate Similarity NPC100719
0.8485 Intermediate Similarity NPC166791
0.8261 Intermediate Similarity NPC67183
0.8219 Intermediate Similarity NPC169095
0.8169 Intermediate Similarity NPC213223
0.8116 Intermediate Similarity NPC67608
0.8088 Intermediate Similarity NPC278895
0.803 Intermediate Similarity NPC155849
0.8 Intermediate Similarity NPC122521
0.8 Intermediate Similarity NPC174447
0.8 Intermediate Similarity NPC251042
0.7973 Intermediate Similarity NPC198240
0.7971 Intermediate Similarity NPC476614
0.7969 Intermediate Similarity NPC34416
0.7887 Intermediate Similarity NPC29328
0.7879 Intermediate Similarity NPC40082
0.7867 Intermediate Similarity NPC469617
0.7857 Intermediate Similarity NPC143396
0.7838 Intermediate Similarity NPC61952
0.7838 Intermediate Similarity NPC316324
0.7808 Intermediate Similarity NPC472327
0.7778 Intermediate Similarity NPC35656
0.7761 Intermediate Similarity NPC322457
0.7733 Intermediate Similarity NPC192006
0.7733 Intermediate Similarity NPC108816
0.7733 Intermediate Similarity NPC93763
0.7714 Intermediate Similarity NPC313444
0.7671 Intermediate Similarity NPC227396
0.7662 Intermediate Similarity NPC325031
0.7656 Intermediate Similarity NPC18951
0.7656 Intermediate Similarity NPC325977
0.7647 Intermediate Similarity NPC234767
0.7647 Intermediate Similarity NPC150162
0.7647 Intermediate Similarity NPC470325
0.7647 Intermediate Similarity NPC53642
0.7625 Intermediate Similarity NPC122502
0.7612 Intermediate Similarity NPC125312
0.7612 Intermediate Similarity NPC174560
0.76 Intermediate Similarity NPC116177
0.76 Intermediate Similarity NPC97377
0.76 Intermediate Similarity NPC320630
0.76 Intermediate Similarity NPC7563
0.76 Intermediate Similarity NPC180290
0.7595 Intermediate Similarity NPC14575
0.7595 Intermediate Similarity NPC196487
0.7576 Intermediate Similarity NPC274927
0.7576 Intermediate Similarity NPC106851
0.7571 Intermediate Similarity NPC472875
0.7568 Intermediate Similarity NPC476795
0.7538 Intermediate Similarity NPC225929
0.7536 Intermediate Similarity NPC136164
0.7536 Intermediate Similarity NPC255863
0.7536 Intermediate Similarity NPC245947
0.7532 Intermediate Similarity NPC271104
0.75 Intermediate Similarity NPC476627
0.75 Intermediate Similarity NPC315597
0.75 Intermediate Similarity NPC190049
0.75 Intermediate Similarity NPC316029
0.75 Intermediate Similarity NPC267231
0.7468 Intermediate Similarity NPC97913
0.7468 Intermediate Similarity NPC49019
0.7467 Intermediate Similarity NPC61863
0.7463 Intermediate Similarity NPC235242
0.7463 Intermediate Similarity NPC472328
0.746 Intermediate Similarity NPC36061
0.746 Intermediate Similarity NPC1813
0.746 Intermediate Similarity NPC321062
0.746 Intermediate Similarity NPC294548
0.746 Intermediate Similarity NPC139029
0.746 Intermediate Similarity NPC70387
0.7439 Intermediate Similarity NPC72397
0.7432 Intermediate Similarity NPC3753
0.7432 Intermediate Similarity NPC237591
0.7432 Intermediate Similarity NPC301065
0.7424 Intermediate Similarity NPC471619
0.7419 Intermediate Similarity NPC48162
0.7407 Intermediate Similarity NPC234038
0.7407 Intermediate Similarity NPC164393
0.7403 Intermediate Similarity NPC476624
0.7403 Intermediate Similarity NPC472013
0.7397 Intermediate Similarity NPC67076
0.7397 Intermediate Similarity NPC319163
0.7375 Intermediate Similarity NPC472864
0.7375 Intermediate Similarity NPC164577
0.7375 Intermediate Similarity NPC19849
0.7375 Intermediate Similarity NPC472865
0.7375 Intermediate Similarity NPC248758
0.7368 Intermediate Similarity NPC86917
0.7368 Intermediate Similarity NPC472014
0.7361 Intermediate Similarity NPC236208
0.7361 Intermediate Similarity NPC469914
0.7353 Intermediate Similarity NPC64985
0.7349 Intermediate Similarity NPC212598
0.7344 Intermediate Similarity NPC32467
0.7344 Intermediate Similarity NPC322461
0.7344 Intermediate Similarity NPC87564
0.7344 Intermediate Similarity NPC424
0.7344 Intermediate Similarity NPC474127
0.7344 Intermediate Similarity NPC281972
0.7344 Intermediate Similarity NPC85813
0.7344 Intermediate Similarity NPC25417
0.7344 Intermediate Similarity NPC290563
0.7344 Intermediate Similarity NPC261831
0.7344 Intermediate Similarity NPC154245
0.7344 Intermediate Similarity NPC88966
0.7344 Intermediate Similarity NPC6095
0.7342 Intermediate Similarity NPC85772
0.7342 Intermediate Similarity NPC474291
0.7333 Intermediate Similarity NPC329852
0.7333 Intermediate Similarity NPC476844
0.7333 Intermediate Similarity NPC244166
0.7333 Intermediate Similarity NPC68624
0.7324 Intermediate Similarity NPC254886
0.7313 Intermediate Similarity NPC329550
0.7308 Intermediate Similarity NPC474510
0.7302 Intermediate Similarity NPC281245
0.7297 Intermediate Similarity NPC215745
0.7297 Intermediate Similarity NPC275098
0.7297 Intermediate Similarity NPC238948
0.7297 Intermediate Similarity NPC12815
0.7286 Intermediate Similarity NPC326268
0.7286 Intermediate Similarity NPC318420
0.7284 Intermediate Similarity NPC261380
0.7273 Intermediate Similarity NPC59436
0.7273 Intermediate Similarity NPC315765
0.7273 Intermediate Similarity NPC74410
0.7273 Intermediate Similarity NPC196653
0.7273 Intermediate Similarity NPC475994
0.7273 Intermediate Similarity NPC239098
0.7273 Intermediate Similarity NPC471465
0.726 Intermediate Similarity NPC315285
0.725 Intermediate Similarity NPC40746
0.725 Intermediate Similarity NPC250315
0.725 Intermediate Similarity NPC65350
0.725 Intermediate Similarity NPC169575
0.725 Intermediate Similarity NPC102197
0.7237 Intermediate Similarity NPC180886
0.7237 Intermediate Similarity NPC309399
0.7237 Intermediate Similarity NPC279537
0.7237 Intermediate Similarity NPC12740
0.7237 Intermediate Similarity NPC110461
0.7231 Intermediate Similarity NPC473863
0.7231 Intermediate Similarity NPC274290
0.7231 Intermediate Similarity NPC188789
0.7229 Intermediate Similarity NPC473658
0.7222 Intermediate Similarity NPC476629
0.7222 Intermediate Similarity NPC53302
0.7215 Intermediate Similarity NPC40228
0.7215 Intermediate Similarity NPC42470
0.7206 Intermediate Similarity NPC327112
0.72 Intermediate Similarity NPC476355
0.7195 Intermediate Similarity NPC315395
0.7195 Intermediate Similarity NPC305475
0.7195 Intermediate Similarity NPC475461
0.7195 Intermediate Similarity NPC186975
0.7195 Intermediate Similarity NPC316426
0.7195 Intermediate Similarity NPC472869
0.7183 Intermediate Similarity NPC197089
0.7183 Intermediate Similarity NPC315115
0.7176 Intermediate Similarity NPC473986
0.7176 Intermediate Similarity NPC474018
0.7164 Intermediate Similarity NPC329819
0.7162 Intermediate Similarity NPC163003
0.7162 Intermediate Similarity NPC21944
0.7162 Intermediate Similarity NPC133253
0.7162 Intermediate Similarity NPC160817
0.716 Intermediate Similarity NPC476804
0.716 Intermediate Similarity NPC472326
0.716 Intermediate Similarity NPC472958
0.716 Intermediate Similarity NPC472957
0.716 Intermediate Similarity NPC243618
0.716 Intermediate Similarity NPC70424
0.7143 Intermediate Similarity NPC315394
0.7143 Intermediate Similarity NPC118011
0.7143 Intermediate Similarity NPC57744
0.7143 Intermediate Similarity NPC36668
0.7143 Intermediate Similarity NPC471061
0.7143 Intermediate Similarity NPC106040
0.7143 Intermediate Similarity NPC115179
0.7143 Intermediate Similarity NPC107668
0.7143 Intermediate Similarity NPC307092
0.7143 Intermediate Similarity NPC43053
0.7143 Intermediate Similarity NPC470320
0.7143 Intermediate Similarity NPC165711
0.7125 Intermediate Similarity NPC469806
0.7125 Intermediate Similarity NPC471326
0.7125 Intermediate Similarity NPC221231
0.7125 Intermediate Similarity NPC469799
0.7123 Intermediate Similarity NPC265574
0.7121 Intermediate Similarity NPC477201
0.7121 Intermediate Similarity NPC187777
0.7121 Intermediate Similarity NPC179764
0.7108 Intermediate Similarity NPC236618
0.7108 Intermediate Similarity NPC160138
0.7108 Intermediate Similarity NPC475678
0.7108 Intermediate Similarity NPC476409
0.7108 Intermediate Similarity NPC472614

  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 NPC142423 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.76 Intermediate Similarity NPD4756 Discovery
0.746 Intermediate Similarity NPD3172 Approved
0.7344 Intermediate Similarity NPD3194 Approved
0.7344 Intermediate Similarity NPD3196 Approved
0.7344 Intermediate Similarity NPD3195 Phase 2
0.7344 Intermediate Similarity NPD4266 Approved
0.7206 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD7331 Phase 2
0.7101 Intermediate Similarity NPD4194 Approved
0.7101 Intermediate Similarity NPD4193 Approved
0.7101 Intermediate Similarity NPD4192 Approved
0.7101 Intermediate Similarity NPD4191 Approved
0.7097 Intermediate Similarity NPD3173 Approved
0.7097 Intermediate Similarity NPD4220 Pre-registration
0.7073 Intermediate Similarity NPD5363 Approved
0.6883 Remote Similarity NPD8039 Approved
0.6875 Remote Similarity NPD29 Approved
0.6875 Remote Similarity NPD28 Approved
0.6835 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7154 Phase 3
0.6829 Remote Similarity NPD5362 Discontinued
0.6806 Remote Similarity NPD7341 Phase 2
0.6761 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4269 Approved
0.6707 Remote Similarity NPD4270 Approved
0.6707 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6667 Remote Similarity NPD622 Approved
0.6667 Remote Similarity NPD5785 Approved
0.663 Remote Similarity NPD6404 Discontinued
0.6622 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6613 Remote Similarity NPD4222 Approved
0.6613 Remote Similarity NPD3174 Discontinued
0.6591 Remote Similarity NPD7983 Approved
0.6517 Remote Similarity NPD5778 Approved
0.6517 Remote Similarity NPD5779 Approved
0.6477 Remote Similarity NPD6698 Approved
0.6477 Remote Similarity NPD46 Approved
0.6463 Remote Similarity NPD4252 Approved
0.6463 Remote Similarity NPD4819 Approved
0.6463 Remote Similarity NPD4820 Approved
0.6463 Remote Similarity NPD4695 Discontinued
0.6463 Remote Similarity NPD4822 Approved
0.6463 Remote Similarity NPD4821 Approved
0.6438 Remote Similarity NPD3197 Phase 1
0.6429 Remote Similarity NPD5331 Approved
0.6429 Remote Similarity NPD5332 Approved
0.642 Remote Similarity NPD4271 Approved
0.642 Remote Similarity NPD4268 Approved
0.6404 Remote Similarity NPD5284 Approved
0.6404 Remote Similarity NPD5281 Approved
0.6395 Remote Similarity NPD4623 Approved
0.6395 Remote Similarity NPD4519 Discontinued
0.6395 Remote Similarity NPD5786 Approved
0.6386 Remote Similarity NPD4790 Discontinued
0.6364 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6351 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6349 Remote Similarity NPD39 Approved
0.6349 Remote Similarity NPD634 Phase 3
0.631 Remote Similarity NPD5209 Approved
0.6304 Remote Similarity NPD7839 Suspended
0.6292 Remote Similarity NPD7838 Discovery
0.629 Remote Similarity NPD9411 Phase 1
0.6265 Remote Similarity NPD5368 Approved
0.6265 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6264 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6232 Remote Similarity NPD342 Phase 1
0.622 Remote Similarity NPD3732 Approved
0.6207 Remote Similarity NPD4694 Approved
0.6207 Remote Similarity NPD5280 Approved
0.6207 Remote Similarity NPD5279 Phase 3
0.619 Remote Similarity NPD857 Phase 3
0.619 Remote Similarity NPD5369 Approved
0.618 Remote Similarity NPD5346 Phase 2
0.618 Remote Similarity NPD5764 Clinical (unspecified phase)
0.618 Remote Similarity NPD6101 Approved
0.618 Remote Similarity NPD5347 Phase 2
0.617 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6118 Remote Similarity NPD4221 Approved
0.6118 Remote Similarity NPD6435 Approved
0.6118 Remote Similarity NPD4223 Phase 3
0.6105 Remote Similarity NPD2066 Phase 3
0.6092 Remote Similarity NPD1694 Approved
0.6092 Remote Similarity NPD1696 Phase 3
0.6067 Remote Similarity NPD4518 Approved
0.6053 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6044 Remote Similarity NPD7515 Phase 2
0.6044 Remote Similarity NPD6411 Approved
0.6032 Remote Similarity NPD5326 Phase 3
0.6029 Remote Similarity NPD3186 Phase 1
0.6023 Remote Similarity NPD5690 Phase 2
0.6022 Remote Similarity NPD1698 Clinical (unspecified phase)
0.602 Remote Similarity NPD5909 Discontinued
0.6 Remote Similarity NPD800 Approved
0.5977 Remote Similarity NPD4197 Approved
0.5977 Remote Similarity NPD3665 Phase 1
0.5977 Remote Similarity NPD3666 Approved
0.5977 Remote Similarity NPD3133 Approved
0.5955 Remote Similarity NPD4793 Discontinued
0.5955 Remote Similarity NPD3573 Approved
0.5946 Remote Similarity NPD368 Approved
0.5941 Remote Similarity NPD6831 Clinical (unspecified phase)
0.5934 Remote Similarity NPD1086 Approved
0.5934 Remote Similarity NPD9256 Approved
0.5934 Remote Similarity NPD1089 Approved
0.5934 Remote Similarity NPD1090 Approved
0.5934 Remote Similarity NPD5207 Approved
0.5934 Remote Similarity NPD9258 Approved
0.5934 Remote Similarity NPD4096 Approved
0.5934 Remote Similarity NPD5692 Phase 3
0.593 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5926 Remote Similarity NPD4058 Approved
0.5918 Remote Similarity NPD6647 Phase 2
0.5914 Remote Similarity NPD7748 Approved
0.5909 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5909 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5909 Remote Similarity NPD5329 Approved
0.5882 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5882 Remote Similarity NPD6927 Phase 3
0.5875 Remote Similarity NPD5276 Approved
0.587 Remote Similarity NPD7637 Suspended
0.587 Remote Similarity NPD5694 Approved
0.587 Remote Similarity NPD6050 Approved
0.5851 Remote Similarity NPD5695 Phase 3
0.5846 Remote Similarity NPD4265 Approved
0.5844 Remote Similarity NPD3704 Approved
0.5843 Remote Similarity NPD7334 Approved
0.5843 Remote Similarity NPD4690 Approved
0.5843 Remote Similarity NPD7146 Approved
0.5843 Remote Similarity NPD4693 Phase 3
0.5843 Remote Similarity NPD7521 Approved
0.5843 Remote Similarity NPD6684 Approved
0.5843 Remote Similarity NPD3618 Phase 1
0.5843 Remote Similarity NPD6409 Approved
0.5843 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5843 Remote Similarity NPD4688 Approved
0.5843 Remote Similarity NPD4689 Approved
0.5843 Remote Similarity NPD4138 Approved
0.5843 Remote Similarity NPD5205 Approved
0.5843 Remote Similarity NPD4249 Approved
0.5843 Remote Similarity NPD5330 Approved
0.5833 Remote Similarity NPD4225 Approved
0.5833 Remote Similarity NPD3617 Approved
0.5824 Remote Similarity NPD5370 Suspended
0.5814 Remote Similarity NPD226 Approved
0.5806 Remote Similarity NPD1088 Approved
0.5789 Remote Similarity NPD7614 Phase 1
0.5789 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5778 Remote Similarity NPD4250 Approved
0.5778 Remote Similarity NPD4251 Approved
0.5773 Remote Similarity NPD7639 Approved
0.5773 Remote Similarity NPD7640 Approved
0.5758 Remote Similarity NPD1931 Clinical (unspecified phase)
0.5758 Remote Similarity NPD1930 Approved
0.5758 Remote Similarity NPD1929 Approved
0.575 Remote Similarity NPD4691 Approved
0.5747 Remote Similarity NPD3667 Approved
0.5743 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5732 Remote Similarity NPD4687 Approved
0.5732 Remote Similarity NPD5733 Approved
0.5729 Remote Similarity NPD7902 Approved
0.5729 Remote Similarity NPD6083 Phase 2
0.5729 Remote Similarity NPD6084 Phase 2
0.5728 Remote Similarity NPD6371 Approved
0.5714 Remote Similarity NPD2270 Approved
0.5714 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5737 Approved
0.5714 Remote Similarity NPD6672 Approved
0.5714 Remote Similarity NPD6903 Approved
0.5714 Remote Similarity NPD5208 Approved
0.5699 Remote Similarity NPD6079 Approved
0.5699 Remote Similarity NPD5693 Phase 1
0.5699 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5694 Remote Similarity NPD4219 Approved
0.5686 Remote Similarity NPD6686 Approved
0.5684 Remote Similarity NPD1693 Approved
0.5682 Remote Similarity NPD6110 Phase 1
0.5682 Remote Similarity NPD9491 Approved
0.5673 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5672 Remote Similarity NPD5343 Approved
0.567 Remote Similarity NPD5696 Approved
0.567 Remote Similarity NPD7638 Approved
0.5667 Remote Similarity NPD6422 Discontinued
0.5663 Remote Similarity NPD8264 Approved
0.5652 Remote Similarity NPD6673 Approved
0.5652 Remote Similarity NPD6080 Approved
0.5652 Remote Similarity NPD4753 Phase 2
0.5652 Remote Similarity NPD5328 Approved
0.5652 Remote Similarity NPD1695 Approved
0.5652 Remote Similarity NPD6904 Approved
0.5645 Remote Similarity NPD633 Phase 3
0.5645 Remote Similarity NPD77 Approved
0.5645 Remote Similarity NPD9448 Phase 2
0.5645 Remote Similarity NPD9450 Approved
0.5638 Remote Similarity NPD5133 Approved
0.5638 Remote Similarity NPD6399 Phase 3
0.5634 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5634 Remote Similarity NPD615 Clinical (unspecified phase)
0.5625 Remote Similarity NPD387 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4137 Phase 3
0.5618 Remote Similarity NPD6400 Clinical (unspecified phase)

  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