Structure

Physi-Chem Properties

Molecular Weight:  286.19
Volume:  312.625
LogP:  3.454
LogD:  3.288
LogS:  -2.879
# Rotatable Bonds:  0
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.738
Synthetic Accessibility Score:  4.045
Fsp3:  0.737
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.659
MDCK Permeability:  2.705328370211646e-05
Pgp-inhibitor:  0.957
Pgp-substrate:  0.82
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.864
30% Bioavailability (F30%):  0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.435
Plasma Protein Binding (PPB):  93.02086639404297%
Volume Distribution (VD):  1.722
Pgp-substrate:  5.742505073547363%

ADMET: Metabolism

CYP1A2-inhibitor:  0.224
CYP1A2-substrate:  0.329
CYP2C19-inhibitor:  0.105
CYP2C19-substrate:  0.725
CYP2C9-inhibitor:  0.092
CYP2C9-substrate:  0.065
CYP2D6-inhibitor:  0.421
CYP2D6-substrate:  0.04
CYP3A4-inhibitor:  0.866
CYP3A4-substrate:  0.726

ADMET: Excretion

Clearance (CL):  18.931
Half-life (T1/2):  0.773

ADMET: Toxicity

hERG Blockers:  0.061
Human Hepatotoxicity (H-HT):  0.66
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.815
Maximum Recommended Daily Dose:  0.894
Skin Sensitization:  0.958
Carcinogencity:  0.87
Eye Corrosion:  0.492
Eye Irritation:  0.156
Respiratory Toxicity:  0.986

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

  Natural Product: NPC6434

Natural Product ID:  NPC6434
Common Name*:   (8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-Dimethyl-6,7,8,9,11,12,14,15,16,17-Decahydrocyclopenta[A]Phenanthren-3-One
IUPAC Name:   (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:  
Standard InCHIKey:  RSIHSRDYCUFFLA-DYKIIFRCSA-N
Standard InCHI:  InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-17,21H,3-6,8,10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
SMILES:  C[C@]12C=CC(=O)C=C1CC[C@H]1[C@@H]3CC[C@@H]([C@@]3(C)CC[C@H]21)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL209073
PubChem CID:   13308
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003568] Androstane steroids
          • [CHEMONTID:0001467] Androgens and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23755850]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae 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
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens Ki = 260.0 nM PMID[546426]

☑ 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 NPC6434 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
0.9125 High Similarity NPC329043
0.9125 High Similarity NPC161423
0.9125 High Similarity NPC58841
0.9125 High Similarity NPC33913
0.9125 High Similarity NPC321187
0.9125 High Similarity NPC227064
0.8889 High Similarity NPC472265
0.8831 High Similarity NPC96319
0.8675 High Similarity NPC327115
0.8659 High Similarity NPC85774
0.8659 High Similarity NPC82902
0.8659 High Similarity NPC214043
0.8608 High Similarity NPC477522
0.8608 High Similarity NPC477514
0.8588 High Similarity NPC477943
0.8571 High Similarity NPC93778
0.8571 High Similarity NPC58063
0.8554 High Similarity NPC474218
0.8554 High Similarity NPC22133
0.85 High Similarity NPC1319
0.8452 Intermediate Similarity NPC474732
0.8452 Intermediate Similarity NPC31564
0.8452 Intermediate Similarity NPC474778
0.8452 Intermediate Similarity NPC474733
0.8452 Intermediate Similarity NPC469994
0.8452 Intermediate Similarity NPC145879
0.8434 Intermediate Similarity NPC473246
0.8434 Intermediate Similarity NPC237712
0.8415 Intermediate Similarity NPC193347
0.8415 Intermediate Similarity NPC151519
0.8395 Intermediate Similarity NPC26117
0.8395 Intermediate Similarity NPC472478
0.8391 Intermediate Similarity NPC272746
0.8372 Intermediate Similarity NPC2983
0.8372 Intermediate Similarity NPC310010
0.8372 Intermediate Similarity NPC326627
0.8354 Intermediate Similarity NPC129165
0.8354 Intermediate Similarity NPC321016
0.8354 Intermediate Similarity NPC107059
0.8354 Intermediate Similarity NPC134330
0.8354 Intermediate Similarity NPC113733
0.8354 Intermediate Similarity NPC321381
0.8353 Intermediate Similarity NPC317590
0.8353 Intermediate Similarity NPC475740
0.8353 Intermediate Similarity NPC136548
0.8333 Intermediate Similarity NPC470574
0.8333 Intermediate Similarity NPC469948
0.8295 Intermediate Similarity NPC470923
0.8295 Intermediate Similarity NPC474736
0.8295 Intermediate Similarity NPC250575
0.8276 Intermediate Similarity NPC320026
0.8256 Intermediate Similarity NPC328539
0.8256 Intermediate Similarity NPC328313
0.825 Intermediate Similarity NPC155986
0.825 Intermediate Similarity NPC198968
0.825 Intermediate Similarity NPC318495
0.8235 Intermediate Similarity NPC475022
0.8235 Intermediate Similarity NPC20688
0.8235 Intermediate Similarity NPC222613
0.8235 Intermediate Similarity NPC118648
0.8228 Intermediate Similarity NPC162742
0.8228 Intermediate Similarity NPC136188
0.8228 Intermediate Similarity NPC230301
0.8228 Intermediate Similarity NPC304309
0.8228 Intermediate Similarity NPC141071
0.8228 Intermediate Similarity NPC471723
0.8228 Intermediate Similarity NPC28657
0.8228 Intermediate Similarity NPC257347
0.8228 Intermediate Similarity NPC288035
0.8228 Intermediate Similarity NPC22105
0.8228 Intermediate Similarity NPC285893
0.8228 Intermediate Similarity NPC134847
0.8214 Intermediate Similarity NPC144258
0.8214 Intermediate Similarity NPC59453
0.8214 Intermediate Similarity NPC221758
0.8205 Intermediate Similarity NPC471799
0.8205 Intermediate Similarity NPC474140
0.8202 Intermediate Similarity NPC111015
0.8193 Intermediate Similarity NPC470614
0.8193 Intermediate Similarity NPC1272
0.8182 Intermediate Similarity NPC475806
0.8171 Intermediate Similarity NPC164840
0.8171 Intermediate Similarity NPC241290
0.8171 Intermediate Similarity NPC234193
0.8171 Intermediate Similarity NPC209944
0.8171 Intermediate Similarity NPC2482
0.8161 Intermediate Similarity NPC31985
0.8161 Intermediate Similarity NPC472240
0.8161 Intermediate Similarity NPC473999
0.8161 Intermediate Similarity NPC119416
0.8161 Intermediate Similarity NPC268406
0.8161 Intermediate Similarity NPC262858
0.8161 Intermediate Similarity NPC146554
0.8161 Intermediate Similarity NPC1015
0.8161 Intermediate Similarity NPC186688
0.8161 Intermediate Similarity NPC76879
0.8161 Intermediate Similarity NPC26959
0.8161 Intermediate Similarity NPC309603
0.8152 Intermediate Similarity NPC144956
0.8148 Intermediate Similarity NPC473943
0.8148 Intermediate Similarity NPC76931
0.8148 Intermediate Similarity NPC307965
0.8148 Intermediate Similarity NPC18603
0.8148 Intermediate Similarity NPC474216
0.8148 Intermediate Similarity NPC87604
0.814 Intermediate Similarity NPC141292
0.814 Intermediate Similarity NPC475772
0.814 Intermediate Similarity NPC89747
0.8125 Intermediate Similarity NPC244488
0.8125 Intermediate Similarity NPC240604
0.8125 Intermediate Similarity NPC247325
0.8125 Intermediate Similarity NPC470362
0.8125 Intermediate Similarity NPC300324
0.8125 Intermediate Similarity NPC189883
0.8118 Intermediate Similarity NPC323765
0.8118 Intermediate Similarity NPC476426
0.8118 Intermediate Similarity NPC29447
0.8118 Intermediate Similarity NPC471224
0.8118 Intermediate Similarity NPC318390
0.8101 Intermediate Similarity NPC471797
0.8095 Intermediate Similarity NPC477818
0.809 Intermediate Similarity NPC474807
0.809 Intermediate Similarity NPC109305
0.809 Intermediate Similarity NPC233118
0.8077 Intermediate Similarity NPC242001
0.8072 Intermediate Similarity NPC6663
0.8072 Intermediate Similarity NPC47761
0.8072 Intermediate Similarity NPC121984
0.8072 Intermediate Similarity NPC264245
0.8068 Intermediate Similarity NPC48010
0.8068 Intermediate Similarity NPC191684
0.8068 Intermediate Similarity NPC85173
0.8068 Intermediate Similarity NPC126993
0.8068 Intermediate Similarity NPC171441
0.8049 Intermediate Similarity NPC47982
0.8049 Intermediate Similarity NPC209430
0.8049 Intermediate Similarity NPC143182
0.8049 Intermediate Similarity NPC109546
0.8049 Intermediate Similarity NPC30986
0.8049 Intermediate Similarity NPC28862
0.8049 Intermediate Similarity NPC84694
0.8049 Intermediate Similarity NPC328714
0.8049 Intermediate Similarity NPC472490
0.8049 Intermediate Similarity NPC81306
0.8046 Intermediate Similarity NPC292491
0.8046 Intermediate Similarity NPC310752
0.8046 Intermediate Similarity NPC471722
0.8026 Intermediate Similarity NPC197805
0.8025 Intermediate Similarity NPC214570
0.8025 Intermediate Similarity NPC470428
0.8025 Intermediate Similarity NPC34019
0.8023 Intermediate Similarity NPC51014
0.8023 Intermediate Similarity NPC72133
0.8023 Intermediate Similarity NPC194417
0.8023 Intermediate Similarity NPC195640
0.8023 Intermediate Similarity NPC94666
0.8 Intermediate Similarity NPC8993
0.8 Intermediate Similarity NPC209802
0.8 Intermediate Similarity NPC124172
0.7979 Intermediate Similarity NPC87351
0.7978 Intermediate Similarity NPC19114
0.7978 Intermediate Similarity NPC131872
0.7978 Intermediate Similarity NPC185936
0.7978 Intermediate Similarity NPC154101
0.7978 Intermediate Similarity NPC473998
0.7978 Intermediate Similarity NPC168027
0.7976 Intermediate Similarity NPC201852
0.7976 Intermediate Similarity NPC20853
0.7976 Intermediate Similarity NPC50964
0.7976 Intermediate Similarity NPC49964
0.7975 Intermediate Similarity NPC182717
0.7955 Intermediate Similarity NPC86319
0.7955 Intermediate Similarity NPC275740
0.7952 Intermediate Similarity NPC476809
0.7952 Intermediate Similarity NPC236112
0.7949 Intermediate Similarity NPC475728
0.7949 Intermediate Similarity NPC145498
0.7935 Intermediate Similarity NPC108078
0.7935 Intermediate Similarity NPC18509
0.7931 Intermediate Similarity NPC472484
0.7931 Intermediate Similarity NPC472481
0.7931 Intermediate Similarity NPC472482
0.7931 Intermediate Similarity NPC90652
0.7927 Intermediate Similarity NPC275910
0.7927 Intermediate Similarity NPC244385
0.7927 Intermediate Similarity NPC82635
0.7927 Intermediate Similarity NPC6978
0.7927 Intermediate Similarity NPC476949
0.7927 Intermediate Similarity NPC167037
0.7927 Intermediate Similarity NPC285761
0.7927 Intermediate Similarity NPC138621
0.7922 Intermediate Similarity NPC160209
0.7912 Intermediate Similarity NPC472932
0.7912 Intermediate Similarity NPC472824
0.7907 Intermediate Similarity NPC474189
0.7907 Intermediate Similarity NPC474349
0.7907 Intermediate Similarity NPC474083
0.7901 Intermediate Similarity NPC202642
0.7901 Intermediate Similarity NPC73875
0.7901 Intermediate Similarity NPC46160

  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 NPC6434 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
0.9221 High Similarity NPD4195 Approved
0.9125 High Similarity NPD3665 Phase 1
0.9125 High Similarity NPD3133 Approved
0.9125 High Similarity NPD3666 Approved
0.8831 High Similarity NPD3701 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD3618 Phase 1
0.8415 Intermediate Similarity NPD4223 Phase 3
0.8415 Intermediate Similarity NPD4221 Approved
0.8415 Intermediate Similarity NPD3667 Approved
0.8391 Intermediate Similarity NPD6079 Approved
0.8372 Intermediate Similarity NPD4753 Phase 2
0.8315 Intermediate Similarity NPD5210 Approved
0.8315 Intermediate Similarity NPD4629 Approved
0.8295 Intermediate Similarity NPD4202 Approved
0.8235 Intermediate Similarity NPD5690 Phase 2
0.8228 Intermediate Similarity NPD6942 Approved
0.8228 Intermediate Similarity NPD7339 Approved
0.8214 Intermediate Similarity NPD4786 Approved
0.8214 Intermediate Similarity NPD4197 Approved
0.8161 Intermediate Similarity NPD5328 Approved
0.8152 Intermediate Similarity NPD5286 Approved
0.8152 Intermediate Similarity NPD5285 Approved
0.8152 Intermediate Similarity NPD4696 Approved
0.8118 Intermediate Similarity NPD5329 Approved
0.8101 Intermediate Similarity NPD4785 Approved
0.8101 Intermediate Similarity NPD4784 Approved
0.8077 Intermediate Similarity NPD4243 Approved
0.8065 Intermediate Similarity NPD5223 Approved
0.8023 Intermediate Similarity NPD6684 Approved
0.8023 Intermediate Similarity NPD4693 Phase 3
0.8023 Intermediate Similarity NPD4690 Approved
0.8023 Intermediate Similarity NPD7334 Approved
0.8023 Intermediate Similarity NPD4688 Approved
0.8023 Intermediate Similarity NPD5205 Approved
0.8023 Intermediate Similarity NPD4689 Approved
0.8023 Intermediate Similarity NPD7146 Approved
0.8023 Intermediate Similarity NPD5279 Phase 3
0.8023 Intermediate Similarity NPD7521 Approved
0.8023 Intermediate Similarity NPD6409 Approved
0.8023 Intermediate Similarity NPD4138 Approved
0.8023 Intermediate Similarity NPD5330 Approved
0.8022 Intermediate Similarity NPD5221 Approved
0.8022 Intermediate Similarity NPD5222 Approved
0.8022 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7979 Intermediate Similarity NPD5225 Approved
0.7979 Intermediate Similarity NPD5211 Phase 2
0.7979 Intermediate Similarity NPD4633 Approved
0.7979 Intermediate Similarity NPD5224 Approved
0.7979 Intermediate Similarity NPD5226 Approved
0.7935 Intermediate Similarity NPD5173 Approved
0.7935 Intermediate Similarity NPD4755 Approved
0.7895 Intermediate Similarity NPD5175 Approved
0.7895 Intermediate Similarity NPD5174 Approved
0.7882 Intermediate Similarity NPD4788 Approved
0.7849 Intermediate Similarity NPD5290 Discontinued
0.7841 Intermediate Similarity NPD6903 Approved
0.7841 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD4694 Approved
0.7816 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD5280 Approved
0.7812 Intermediate Similarity NPD5141 Approved
0.7778 Intermediate Similarity NPD4190 Phase 3
0.7778 Intermediate Similarity NPD5275 Approved
0.7766 Intermediate Similarity NPD4700 Approved
0.7742 Intermediate Similarity NPD6084 Phase 2
0.7742 Intermediate Similarity NPD6083 Phase 2
0.7738 Intermediate Similarity NPD7525 Registered
0.7727 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD3617 Approved
0.7654 Intermediate Similarity NPD6926 Approved
0.7654 Intermediate Similarity NPD6924 Approved
0.7653 Intermediate Similarity NPD5697 Approved
0.7634 Intermediate Similarity NPD4697 Phase 3
0.7586 Intermediate Similarity NPD3668 Phase 3
0.7582 Intermediate Similarity NPD5284 Approved
0.7582 Intermediate Similarity NPD5281 Approved
0.7576 Intermediate Similarity NPD6011 Approved
0.7576 Intermediate Similarity NPD6881 Approved
0.7576 Intermediate Similarity NPD6899 Approved
0.7576 Intermediate Similarity NPD4729 Approved
0.7576 Intermediate Similarity NPD4730 Approved
0.7529 Intermediate Similarity NPD4695 Discontinued
0.7529 Intermediate Similarity NPD4748 Discontinued
0.7527 Intermediate Similarity NPD5695 Phase 3
0.7526 Intermediate Similarity NPD4754 Approved
0.75 Intermediate Similarity NPD6013 Approved
0.75 Intermediate Similarity NPD7143 Approved
0.75 Intermediate Similarity NPD6012 Approved
0.75 Intermediate Similarity NPD7144 Approved
0.75 Intermediate Similarity NPD6014 Approved
0.75 Intermediate Similarity NPD4691 Approved
0.7474 Intermediate Similarity NPD5696 Approved
0.747 Intermediate Similarity NPD6933 Approved
0.7439 Intermediate Similarity NPD4058 Approved
0.7426 Intermediate Similarity NPD5250 Approved
0.7426 Intermediate Similarity NPD7290 Approved
0.7426 Intermediate Similarity NPD7102 Approved
0.7426 Intermediate Similarity NPD5169 Approved
0.7426 Intermediate Similarity NPD5248 Approved
0.7426 Intermediate Similarity NPD6883 Approved
0.7426 Intermediate Similarity NPD5247 Approved
0.7426 Intermediate Similarity NPD5249 Phase 3
0.7426 Intermediate Similarity NPD5135 Approved
0.7426 Intermediate Similarity NPD4634 Approved
0.7426 Intermediate Similarity NPD5251 Approved
0.7426 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD4519 Discontinued
0.7416 Intermediate Similarity NPD4623 Approved
0.7412 Intermediate Similarity NPD7645 Phase 2
0.7407 Intermediate Similarity NPD7151 Approved
0.7407 Intermediate Similarity NPD7150 Approved
0.7407 Intermediate Similarity NPD7152 Approved
0.74 Intermediate Similarity NPD5128 Approved
0.7391 Intermediate Similarity NPD7515 Phase 2
0.7375 Intermediate Similarity NPD6922 Approved
0.7375 Intermediate Similarity NPD6923 Approved
0.7375 Intermediate Similarity NPD4137 Phase 3
0.7374 Intermediate Similarity NPD7128 Approved
0.7374 Intermediate Similarity NPD4767 Approved
0.7374 Intermediate Similarity NPD4768 Approved
0.7374 Intermediate Similarity NPD5739 Approved
0.7374 Intermediate Similarity NPD6675 Approved
0.7374 Intermediate Similarity NPD6402 Approved
0.7353 Intermediate Similarity NPD5127 Approved
0.7353 Intermediate Similarity NPD6847 Approved
0.7353 Intermediate Similarity NPD8130 Phase 1
0.7353 Intermediate Similarity NPD5215 Approved
0.7353 Intermediate Similarity NPD5217 Approved
0.7353 Intermediate Similarity NPD6617 Approved
0.7353 Intermediate Similarity NPD6869 Approved
0.7353 Intermediate Similarity NPD6649 Approved
0.7353 Intermediate Similarity NPD5216 Approved
0.7353 Intermediate Similarity NPD6650 Approved
0.7312 Intermediate Similarity NPD6399 Phase 3
0.73 Intermediate Similarity NPD5701 Approved
0.73 Intermediate Similarity NPD6412 Phase 2
0.7292 Intermediate Similarity NPD7638 Approved
0.7284 Intermediate Similarity NPD4747 Approved
0.7283 Intermediate Similarity NPD4096 Approved
0.7282 Intermediate Similarity NPD6882 Approved
0.7282 Intermediate Similarity NPD8297 Approved
0.7253 Intermediate Similarity NPD6672 Approved
0.7253 Intermediate Similarity NPD5208 Approved
0.7253 Intermediate Similarity NPD5737 Approved
0.7253 Intermediate Similarity NPD4518 Approved
0.7245 Intermediate Similarity NPD5091 Approved
0.7241 Intermediate Similarity NPD4692 Approved
0.7241 Intermediate Similarity NPD4139 Approved
0.7228 Intermediate Similarity NPD7320 Approved
0.7228 Intermediate Similarity NPD5168 Approved
0.7216 Intermediate Similarity NPD7639 Approved
0.7216 Intermediate Similarity NPD7640 Approved
0.7212 Intermediate Similarity NPD4632 Approved
0.7209 Intermediate Similarity NPD6929 Approved
0.7176 Intermediate Similarity NPD6932 Approved
0.7174 Intermediate Similarity NPD6051 Approved
0.7174 Intermediate Similarity NPD6904 Approved
0.7174 Intermediate Similarity NPD6673 Approved
0.7174 Intermediate Similarity NPD6080 Approved
0.716 Intermediate Similarity NPD3698 Phase 2
0.7157 Intermediate Similarity NPD6373 Approved
0.7157 Intermediate Similarity NPD6372 Approved
0.7143 Intermediate Similarity NPD5167 Approved
0.7128 Intermediate Similarity NPD5133 Approved
0.7126 Intermediate Similarity NPD6930 Phase 2
0.7126 Intermediate Similarity NPD6931 Approved
0.7097 Intermediate Similarity NPD5207 Approved
0.7093 Intermediate Similarity NPD7145 Approved
0.7073 Intermediate Similarity NPD4245 Approved
0.7073 Intermediate Similarity NPD4244 Approved
0.7053 Intermediate Similarity NPD7748 Approved
0.7033 Intermediate Similarity NPD6098 Approved
0.7024 Intermediate Similarity NPD4687 Approved
0.7021 Intermediate Similarity NPD5693 Phase 1
0.7021 Intermediate Similarity NPD5694 Approved
0.7019 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6009 Approved
0.7009 Intermediate Similarity NPD6317 Approved
0.6979 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6977 Remote Similarity NPD5776 Phase 2
0.6977 Remote Similarity NPD6925 Approved
0.6944 Remote Similarity NPD6335 Approved
0.6944 Remote Similarity NPD6314 Approved
0.6944 Remote Similarity NPD6313 Approved
0.6932 Remote Similarity NPD7509 Discontinued
0.6932 Remote Similarity NPD7514 Phase 3
0.6923 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6916 Remote Similarity NPD6274 Approved
0.6915 Remote Similarity NPD5692 Phase 3
0.6897 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6889 Remote Similarity NPD6695 Phase 3
0.6882 Remote Similarity NPD4723 Approved
0.6882 Remote Similarity NPD4722 Approved
0.6881 Remote Similarity NPD4522 Approved
0.6881 Remote Similarity NPD7101 Approved
0.6881 Remote Similarity NPD7100 Approved
0.6875 Remote Similarity NPD6001 Approved
0.6854 Remote Similarity NPD6902 Approved
0.6842 Remote Similarity NPD6050 Approved
0.6837 Remote Similarity NPD7902 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