Structure

Physi-Chem Properties

Molecular Weight:  608.27
Volume:  605.363
LogP:  4.233
LogD:  3.714
LogS:  -5.269
# Rotatable Bonds:  10
TPSA:  117.78
# H-Bond Aceptor:  11
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.374
Synthetic Accessibility Score:  4.342
Fsp3:  0.515
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.087
MDCK Permeability:  4.7696219553472474e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.03
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.962
Plasma Protein Binding (PPB):  80.33744049072266%
Volume Distribution (VD):  0.745
Pgp-substrate:  18.852031707763672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.037
CYP1A2-substrate:  0.972
CYP2C19-inhibitor:  0.157
CYP2C19-substrate:  0.907
CYP2C9-inhibitor:  0.119
CYP2C9-substrate:  0.662
CYP2D6-inhibitor:  0.257
CYP2D6-substrate:  0.891
CYP3A4-inhibitor:  0.776
CYP3A4-substrate:  0.926

ADMET: Excretion

Clearance (CL):  8.711
Half-life (T1/2):  0.552

ADMET: Toxicity

hERG Blockers:  0.91
Human Hepatotoxicity (H-HT):  0.189
Drug-inuced Liver Injury (DILI):  0.926
AMES Toxicity:  0.032
Rat Oral Acute Toxicity:  0.583
Maximum Recommended Daily Dose:  0.973
Skin Sensitization:  0.163
Carcinogencity:  0.037
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.965

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

  Natural Product: NPC100734

Natural Product ID:  NPC100734
Common Name*:   Methyl (1S,15R,17S,18S,19R,20R)-6,18-Dimethoxy-17-(3,4,5-Trimethoxybenzoyl)Oxy-1,3,11,12,14,15,16,17,18,19,20,21-Dodecahydroyohimban-19-Carboxylate
IUPAC Name:   methyl (1S,15R,17S,18S,19R,20R)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Synonyms:  
Standard InCHIKey:  QEVHRUUCFGRFIF-KWTXYEQSSA-N
Standard InCHI:  InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m0/s1
SMILES:  COc1ccc2c3CCN4C[C@@H]5C[C@@H]([C@H]([C@@H]([C@@H]5C[C@H]4c3[nH]c2c1)C(=O)OC)OC)OC(=O)c1cc(c(c(c1)OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1396912
PubChem CID:   6604180
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001786] Yohimbine alkaloids

*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
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. DOI[10.1078/0176-1617-00195]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[10757735]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[14735439]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. callus n.a. PMID[15715262]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[18220354]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[28445039]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota Roots n.a. n.a. PMID[30024167]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7282 Rauvolfia serpentina Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7282 Rauvolfia serpentina Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7282 Rauvolfia serpentina Species Apocynaceae 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
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 10000.0 nM PMID[480083]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 15848.9 nM PMID[480083]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 17782.8 nM PMID[480083]
NPT211 Individual Protein Hypoxia-inducible factor 1 alpha Homo sapiens Potency = 10000.0 nM PMID[480083]
NPT45 Individual Protein Ubiquitin carboxyl-terminal hydrolase 2 Homo sapiens Potency = 10000.0 nM PMID[480083]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 12589.3 nM PMID[480083]
NPT2930 Individual Protein Hemoglobin beta chain Homo sapiens Potency = 15848.9 nM PMID[480083]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 7943.3 nM PMID[480083]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 8912.5 nM PMID[480083]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 7943.28 nM PMID[480083]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 15848.93 nM PMID[480083]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 31622.8 nM PMID[480083]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 14125.4 nM PMID[480083]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 1412.5 nM PMID[480083]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 6309.6 nM PMID[480083]

☑ 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 NPC100734 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 NPC315634
1.0 High Similarity NPC88923
0.9827 High Similarity NPC191489
0.9784 High Similarity NPC284685
0.8534 High Similarity NPC21638
0.819 Intermediate Similarity NPC148183
0.819 Intermediate Similarity NPC152768
0.8178 Intermediate Similarity NPC471303
0.7984 Intermediate Similarity NPC473105
0.7975 Intermediate Similarity NPC472099
0.7942 Intermediate Similarity NPC476429
0.7924 Intermediate Similarity NPC169402
0.7909 Intermediate Similarity NPC237901
0.7909 Intermediate Similarity NPC195788
0.7903 Intermediate Similarity NPC113455
0.7891 Intermediate Similarity NPC89549
0.788 Intermediate Similarity NPC120239
0.7839 Intermediate Similarity NPC116238
0.7804 Intermediate Similarity NPC303374
0.7796 Intermediate Similarity NPC474192
0.7796 Intermediate Similarity NPC475720
0.779 Intermediate Similarity NPC260909
0.7773 Intermediate Similarity NPC478083
0.7773 Intermediate Similarity NPC318068
0.7769 Intermediate Similarity NPC81939
0.7755 Intermediate Similarity NPC476999
0.7755 Intermediate Similarity NPC474688
0.7754 Intermediate Similarity NPC264176
0.7751 Intermediate Similarity NPC304837
0.7751 Intermediate Similarity NPC476258
0.775 Intermediate Similarity NPC174760
0.7741 Intermediate Similarity NPC473041
0.7738 Intermediate Similarity NPC475666
0.7737 Intermediate Similarity NPC476436
0.7729 Intermediate Similarity NPC188400
0.772 Intermediate Similarity NPC475844
0.7713 Intermediate Similarity NPC129897
0.7708 Intermediate Similarity NPC1608
0.7702 Intermediate Similarity NPC154922
0.7698 Intermediate Similarity NPC124313
0.7692 Intermediate Similarity NPC4687
0.7686 Intermediate Similarity NPC280272
0.7683 Intermediate Similarity NPC217176
0.768 Intermediate Similarity NPC475816
0.7671 Intermediate Similarity NPC184680
0.7667 Intermediate Similarity NPC46561
0.7661 Intermediate Similarity NPC90875
0.7649 Intermediate Similarity NPC119134
0.7645 Intermediate Similarity NPC198503
0.764 Intermediate Similarity NPC470785
0.7636 Intermediate Similarity NPC472589
0.7633 Intermediate Similarity NPC478078
0.7625 Intermediate Similarity NPC305984
0.7619 Intermediate Similarity NPC84164
0.7619 Intermediate Similarity NPC207283
0.7617 Intermediate Similarity NPC473800
0.7605 Intermediate Similarity NPC310211
0.7605 Intermediate Similarity NPC308137
0.7605 Intermediate Similarity NPC472098
0.7602 Intermediate Similarity NPC311906
0.7597 Intermediate Similarity NPC478080
0.7593 Intermediate Similarity NPC96321
0.759 Intermediate Similarity NPC207620
0.759 Intermediate Similarity NPC160113
0.759 Intermediate Similarity NPC476220
0.7586 Intermediate Similarity NPC254240
0.7586 Intermediate Similarity NPC128265
0.7586 Intermediate Similarity NPC312870
0.7586 Intermediate Similarity NPC199851
0.7586 Intermediate Similarity NPC294909
0.7585 Intermediate Similarity NPC473639
0.7581 Intermediate Similarity NPC233334
0.7579 Intermediate Similarity NPC477066
0.757 Intermediate Similarity NPC470784
0.7563 Intermediate Similarity NPC169716
0.7563 Intermediate Similarity NPC87413
0.7558 Intermediate Similarity NPC472588
0.7549 Intermediate Similarity NPC183537
0.7549 Intermediate Similarity NPC181081
0.7549 Intermediate Similarity NPC67401
0.7549 Intermediate Similarity NPC478081
0.7542 Intermediate Similarity NPC249583
0.754 Intermediate Similarity NPC168922
0.7539 Intermediate Similarity NPC270515
0.7531 Intermediate Similarity NPC150239
0.753 Intermediate Similarity NPC471762
0.753 Intermediate Similarity NPC66777
0.751 Intermediate Similarity NPC3207
0.751 Intermediate Similarity NPC203373
0.75 Intermediate Similarity NPC300156
0.75 Intermediate Similarity NPC17437
0.75 Intermediate Similarity NPC280799
0.75 Intermediate Similarity NPC24019
0.749 Intermediate Similarity NPC329982
0.749 Intermediate Similarity NPC52254
0.748 Intermediate Similarity NPC478082
0.748 Intermediate Similarity NPC477067
0.7469 Intermediate Similarity NPC144452
0.746 Intermediate Similarity NPC189903
0.746 Intermediate Similarity NPC476995
0.746 Intermediate Similarity NPC182907
0.746 Intermediate Similarity NPC6786
0.7451 Intermediate Similarity NPC15406
0.745 Intermediate Similarity NPC253675
0.7449 Intermediate Similarity NPC82070
0.7449 Intermediate Similarity NPC469594
0.7449 Intermediate Similarity NPC247803
0.7431 Intermediate Similarity NPC166722
0.7421 Intermediate Similarity NPC108342
0.7421 Intermediate Similarity NPC473187
0.7418 Intermediate Similarity NPC298436
0.7418 Intermediate Similarity NPC208084
0.7413 Intermediate Similarity NPC77878
0.7413 Intermediate Similarity NPC302807
0.7412 Intermediate Similarity NPC473540
0.7412 Intermediate Similarity NPC166712
0.741 Intermediate Similarity NPC329631
0.74 Intermediate Similarity NPC474701
0.7396 Intermediate Similarity NPC132385
0.7393 Intermediate Similarity NPC107123
0.739 Intermediate Similarity NPC274640
0.739 Intermediate Similarity NPC194740
0.7386 Intermediate Similarity NPC215837
0.7383 Intermediate Similarity NPC475648
0.7381 Intermediate Similarity NPC34770
0.7381 Intermediate Similarity NPC39370
0.7375 Intermediate Similarity NPC471304
0.7373 Intermediate Similarity NPC49672
0.7368 Intermediate Similarity NPC475271
0.7364 Intermediate Similarity NPC39679
0.7362 Intermediate Similarity NPC81654
0.7362 Intermediate Similarity NPC49196
0.7362 Intermediate Similarity NPC313985
0.7362 Intermediate Similarity NPC195461
0.7362 Intermediate Similarity NPC249150
0.7362 Intermediate Similarity NPC79129
0.7358 Intermediate Similarity NPC60621
0.7358 Intermediate Similarity NPC477903
0.7355 Intermediate Similarity NPC39500
0.7355 Intermediate Similarity NPC469592
0.7355 Intermediate Similarity NPC471080
0.7353 Intermediate Similarity NPC45190
0.7352 Intermediate Similarity NPC57453
0.7352 Intermediate Similarity NPC295228
0.7349 Intermediate Similarity NPC157931
0.7346 Intermediate Similarity NPC473188
0.7341 Intermediate Similarity NPC470042
0.7341 Intermediate Similarity NPC22481
0.7339 Intermediate Similarity NPC473449
0.7339 Intermediate Similarity NPC477900
0.7339 Intermediate Similarity NPC26881
0.7339 Intermediate Similarity NPC477899
0.7333 Intermediate Similarity NPC253482
0.7331 Intermediate Similarity NPC201508
0.7328 Intermediate Similarity NPC477788
0.7326 Intermediate Similarity NPC58209
0.7325 Intermediate Similarity NPC146976
0.7317 Intermediate Similarity NPC469439
0.7312 Intermediate Similarity NPC327769
0.7308 Intermediate Similarity NPC134637
0.7302 Intermediate Similarity NPC473186
0.73 Intermediate Similarity NPC120513
0.7295 Intermediate Similarity NPC476114
0.7295 Intermediate Similarity NPC330009
0.7293 Intermediate Similarity NPC328928
0.7293 Intermediate Similarity NPC471978
0.7292 Intermediate Similarity NPC475910
0.7291 Intermediate Similarity NPC476996
0.7291 Intermediate Similarity NPC476998
0.7291 Intermediate Similarity NPC91125
0.7288 Intermediate Similarity NPC329747
0.7284 Intermediate Similarity NPC236668
0.7283 Intermediate Similarity NPC473833
0.728 Intermediate Similarity NPC133609
0.728 Intermediate Similarity NPC211920
0.7277 Intermediate Similarity NPC50503
0.7276 Intermediate Similarity NPC471979
0.7273 Intermediate Similarity NPC96584
0.7273 Intermediate Similarity NPC255800
0.727 Intermediate Similarity NPC116701
0.7269 Intermediate Similarity NPC179287
0.7269 Intermediate Similarity NPC97746
0.7269 Intermediate Similarity NPC173250
0.7266 Intermediate Similarity NPC152620
0.7262 Intermediate Similarity NPC316841
0.7262 Intermediate Similarity NPC260434
0.7259 Intermediate Similarity NPC469734
0.7258 Intermediate Similarity NPC235364
0.7258 Intermediate Similarity NPC210434
0.7252 Intermediate Similarity NPC189079
0.7251 Intermediate Similarity NPC476997
0.7251 Intermediate Similarity NPC476994
0.7248 Intermediate Similarity NPC208364
0.7247 Intermediate Similarity NPC225279
0.7244 Intermediate Similarity NPC475406
0.7238 Intermediate Similarity NPC9482
0.7237 Intermediate Similarity NPC210296
0.7237 Intermediate Similarity NPC148889
0.7236 Intermediate Similarity NPC184408
0.7236 Intermediate Similarity NPC303658

  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 NPC100734 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
1.0 High Similarity NPD7803 Approved
0.9827 High Similarity NPD7708 Approved
0.9784 High Similarity NPD7955 Approved
0.9784 High Similarity NPD7956 Approved
0.7942 Intermediate Similarity NPD4885 Approved
0.7909 Intermediate Similarity NPD8467 Approved
0.7909 Intermediate Similarity NPD8465 Approved
0.7909 Intermediate Similarity NPD8466 Approved
0.7905 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD7690 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD5658 Approved
0.779 Intermediate Similarity NPD8460 Approved
0.779 Intermediate Similarity NPD8426 Approved
0.779 Intermediate Similarity NPD8459 Approved
0.779 Intermediate Similarity NPD8425 Approved
0.7787 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7787 Intermediate Similarity NPD5482 Discontinued
0.7774 Intermediate Similarity NPD8427 Approved
0.7774 Intermediate Similarity NPD8429 Approved
0.7774 Intermediate Similarity NPD8428 Approved
0.7743 Intermediate Similarity NPD8091 Phase 3
0.7741 Intermediate Similarity NPD5632 Approved
0.7681 Intermediate Similarity NPD8364 Approved
0.7681 Intermediate Similarity NPD8363 Approved
0.7623 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD7886 Phase 2
0.761 Intermediate Similarity NPD7885 Phase 2
0.7586 Intermediate Similarity NPD4500 Approved
0.7586 Intermediate Similarity NPD4501 Approved
0.7571 Intermediate Similarity NPD4952 Phase 3
0.7559 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD5488 Discontinued
0.751 Intermediate Similarity NPD7417 Discontinued
0.75 Intermediate Similarity NPD8358 Approved
0.75 Intermediate Similarity NPD5450 Discontinued
0.7482 Intermediate Similarity NPD8489 Phase 1
0.748 Intermediate Similarity NPD4373 Phase 2
0.747 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD6716 Phase 1
0.741 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD7859 Phase 2
0.7367 Intermediate Similarity NPD6745 Discontinued
0.7362 Intermediate Similarity NPD4600 Approved
0.7362 Intermediate Similarity NPD4601 Approved
0.7356 Intermediate Similarity NPD8463 Approved
0.7348 Intermediate Similarity NPD6228 Discontinued
0.7344 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7336 Intermediate Similarity NPD8350 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD5902 Approved
0.7325 Intermediate Similarity NPD5903 Approved
0.7321 Intermediate Similarity NPD7862 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD3006 Discontinued
0.7276 Intermediate Similarity NPD1483 Discontinued
0.7262 Intermediate Similarity NPD6962 Phase 2
0.7247 Intermediate Similarity NPD5930 Phase 3
0.7227 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7994 Phase 2
0.7211 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD7194 Discontinued
0.7205 Intermediate Similarity NPD6494 Phase 2
0.7205 Intermediate Similarity NPD6625 Approved
0.7189 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD6242 Discontinued
0.7176 Intermediate Similarity NPD6963 Approved
0.7176 Intermediate Similarity NPD6964 Approved
0.7171 Intermediate Similarity NPD6790 Phase 1
0.7166 Intermediate Similarity NPD7395 Discontinued
0.7165 Intermediate Similarity NPD7797 Approved
0.7165 Intermediate Similarity NPD7796 Approved
0.7137 Intermediate Similarity NPD3003 Approved
0.7137 Intermediate Similarity NPD7558 Phase 2
0.7137 Intermediate Similarity NPD6770 Approved
0.7137 Intermediate Similarity NPD8102 Discontinued
0.7121 Intermediate Similarity NPD5805 Approved
0.7119 Intermediate Similarity NPD4506 Discontinued
0.7103 Intermediate Similarity NPD7426 Phase 1
0.7102 Intermediate Similarity NPD3815 Phase 1
0.7102 Intermediate Similarity NPD3816 Phase 1
0.7101 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7589 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD5293 Phase 2
0.704 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD7069 Discontinued
0.702 Intermediate Similarity NPD5479 Discontinued
0.7016 Intermediate Similarity NPD3394 Approved
0.7016 Intermediate Similarity NPD3393 Approved
0.7016 Intermediate Similarity NPD3389 Approved
0.7016 Intermediate Similarity NPD7853 Phase 2
0.7015 Intermediate Similarity NPD8461 Discontinued
0.7014 Intermediate Similarity NPD7181 Phase 3
0.7011 Intermediate Similarity NPD6517 Phase 3
0.6996 Remote Similarity NPD8359 Phase 2
0.6987 Remote Similarity NPD5071 Phase 2
0.6978 Remote Similarity NPD8255 Phase 2
0.6969 Remote Similarity NPD3263 Phase 3
0.6964 Remote Similarity NPD5866 Approved
0.6963 Remote Similarity NPD6531 Approved
0.6963 Remote Similarity NPD6530 Approved
0.696 Remote Similarity NPD6985 Discontinued
0.6943 Remote Similarity NPD4558 Phase 2
0.6941 Remote Similarity NPD4328 Approved
0.6941 Remote Similarity NPD3259 Approved
0.6939 Remote Similarity NPD2916 Discontinued
0.6933 Remote Similarity NPD4418 Discontinued
0.6933 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6929 Remote Similarity NPD3925 Approved
0.6923 Remote Similarity NPD5416 Discontinued
0.692 Remote Similarity NPD7689 Approved
0.692 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6917 Remote Similarity NPD6243 Phase 3
0.6917 Remote Similarity NPD6244 Phase 3
0.6917 Remote Similarity NPD7588 Discontinued
0.6914 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6908 Remote Similarity NPD3257 Approved
0.6905 Remote Similarity NPD8479 Phase 2
0.6904 Remote Similarity NPD6550 Discontinued
0.6898 Remote Similarity NPD5429 Discontinued
0.6895 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6888 Remote Similarity NPD1768 Approved
0.6887 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6886 Remote Similarity NPD6456 Discontinued
0.6883 Remote Similarity NPD5914 Approved
0.688 Remote Similarity NPD8149 Discontinued
0.6875 Remote Similarity NPD5003 Discontinued
0.6872 Remote Similarity NPD5006 Approved
0.6872 Remote Similarity NPD5005 Approved
0.687 Remote Similarity NPD8016 Phase 3
0.687 Remote Similarity NPD2509 Approved
0.687 Remote Similarity NPD8017 Clinical (unspecified phase)
0.687 Remote Similarity NPD2510 Approved
0.6865 Remote Similarity NPD3258 Approved
0.6862 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6858 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6856 Remote Similarity NPD7620 Phase 2
0.6846 Remote Similarity NPD4987 Clinical (unspecified phase)
0.684 Remote Similarity NPD7538 Clinical (unspecified phase)
0.684 Remote Similarity NPD4897 Phase 2
0.6838 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6838 Remote Similarity NPD8310 Clinical (unspecified phase)
0.683 Remote Similarity NPD6230 Discontinued
0.6829 Remote Similarity NPD7222 Phase 2
0.6825 Remote Similarity NPD7878 Phase 2
0.6824 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6874 Approved
0.6816 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6812 Remote Similarity NPD7924 Phase 2
0.6812 Remote Similarity NPD7925 Phase 2
0.6811 Remote Similarity NPD5506 Approved
0.6811 Remote Similarity NPD5507 Approved
0.681 Remote Similarity NPD3920 Phase 2
0.6801 Remote Similarity NPD8357 Approved
0.6798 Remote Similarity NPD3763 Approved
0.6783 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6779 Remote Similarity NPD8279 Clinical (unspecified phase)
0.6778 Remote Similarity NPD3922 Approved
0.6778 Remote Similarity NPD3924 Approved
0.6778 Remote Similarity NPD3923 Approved
0.6778 Remote Similarity NPD3921 Approved
0.6777 Remote Similarity NPD53 Approved
0.6777 Remote Similarity NPD7778 Approved
0.6777 Remote Similarity NPD7777 Approved
0.677 Remote Similarity NPD7674 Phase 3
0.677 Remote Similarity NPD7676 Clinical (unspecified phase)
0.677 Remote Similarity NPD7675 Phase 3
0.6763 Remote Similarity NPD5512 Phase 3
0.6759 Remote Similarity NPD4429 Discontinued
0.6757 Remote Similarity NPD5022 Discontinued
0.6756 Remote Similarity NPD5891 Approved
0.6746 Remote Similarity NPD5612 Discontinued
0.6743 Remote Similarity NPD6723 Discontinued
0.6742 Remote Similarity NPD6460 Clinical (unspecified phase)
0.6742 Remote Similarity NPD8468 Phase 2
0.6734 Remote Similarity NPD6376 Discontinued
0.6732 Remote Similarity NPD2899 Discontinued
0.6732 Remote Similarity NPD7719 Discontinued
0.6731 Remote Similarity NPD7688 Phase 1
0.673 Remote Similarity NPD4368 Phase 2
0.672 Remote Similarity NPD4502 Phase 2
0.6715 Remote Similarity NPD7673 Phase 3
0.6708 Remote Similarity NPD4420 Approved
0.6707 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6705 Remote Similarity NPD5640 Discontinued
0.6694 Remote Similarity NPD1392 Approved
0.6693 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6693 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6693 Remote Similarity NPD7225 Discontinued
0.6693 Remote Similarity NPD6198 Phase 1
0.6691 Remote Similarity NPD8442 Discontinued
0.6691 Remote Similarity NPD8492 Approved
0.668 Remote Similarity NPD4795 Phase 2
0.6679 Remote Similarity NPD8100 Phase 3
0.6679 Remote Similarity NPD7922 Phase 1
0.6667 Remote Similarity NPD6974 Phase 3
0.6667 Remote Similarity NPD8244 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