Structure

Physi-Chem Properties

Molecular Weight:  334.25
Volume:  367.201
LogP:  3.042
LogD:  2.966
LogS:  -4.205
# Rotatable Bonds:  2
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.806
Synthetic Accessibility Score:  4.924
Fsp3:  0.857
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:  -4.77
MDCK Permeability:  2.875810423574876e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.789
Plasma Protein Binding (PPB):  88.63025665283203%
Volume Distribution (VD):  0.777
Pgp-substrate:  11.205696105957031%

ADMET: Metabolism

CYP1A2-inhibitor:  0.029
CYP1A2-substrate:  0.485
CYP2C19-inhibitor:  0.15
CYP2C19-substrate:  0.874
CYP2C9-inhibitor:  0.245
CYP2C9-substrate:  0.07
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.074
CYP3A4-inhibitor:  0.894
CYP3A4-substrate:  0.72

ADMET: Excretion

Clearance (CL):  5.659
Half-life (T1/2):  0.284

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.288
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.057
Rat Oral Acute Toxicity:  0.121
Maximum Recommended Daily Dose:  0.921
Skin Sensitization:  0.826
Carcinogencity:  0.226
Eye Corrosion:  0.051
Eye Irritation:  0.852
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC476412

Natural Product ID:  NPC476412
Common Name*:   13Beta,18-Dihydroxy-8(14)-Abieten-7-One
IUPAC Name:   (1R,4aR,4bR,7S,10aR)-7-hydroxy-1-(hydroxymethyl)-1,4a,10a-trimethyl-7-propan-2-yl-3,4,4b,5,6,10-hexahydro-2H-phenanthren-9-one
Synonyms:  
Standard InCHIKey:  CIWBMFOZMOATTP-JBINPLMMSA-N
Standard InCHI:  InChI=1S/C21H34O3/c1-14(2)21(24)10-7-16-15(11-21)17(23)12-20(5)18(3,13-22)8-6-9-19(16,20)4/h11,14,16,22,24H,6-10,12-13H2,1-5H3/t16-,18-,19+,20-,21+/m0/s1
SMILES:  OC[C@]1(C)CCC[C@]2([C@@]1(C)CC(=O)C1=C[C@@](CC[C@H]21)(O)C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL597944
PubChem CID:   46230316
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0001757] Colensane and clerodane 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
NPO2882 Abies georgei Species Pinaceae Eukaryota aerial parts Zhongdian city, Yunnan Province of China n.a. PMID[20022253]

☑ 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 100.0 ug.mL-1 PMID[479243]
NPT114 Cell Line LoVo Homo sapiens IC50 > 25.0 ug.mL-1 PMID[479243]
NPT2 Others Unspecified IC50 > 100.0 ug.mL-1 PMID[479243]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 25.0 ug.mL-1 PMID[479243]

☑ 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 NPC476412 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
0.9398 High Similarity NPC472973
0.9231 High Similarity NPC62336
0.9176 High Similarity NPC472978
0.9146 High Similarity NPC476426
0.9036 High Similarity NPC472974
0.9 High Similarity NPC2482
0.8974 High Similarity NPC263582
0.8966 High Similarity NPC472977
0.8966 High Similarity NPC472976
0.8953 High Similarity NPC472975
0.8929 High Similarity NPC476409
0.8875 High Similarity NPC308038
0.8851 High Similarity NPC476416
0.881 High Similarity NPC472986
0.881 High Similarity NPC472985
0.875 High Similarity NPC475994
0.875 High Similarity NPC471409
0.875 High Similarity NPC275494
0.8736 High Similarity NPC475806
0.8721 High Similarity NPC473999
0.8721 High Similarity NPC309603
0.869 High Similarity NPC274724
0.869 High Similarity NPC469948
0.869 High Similarity NPC471224
0.8659 High Similarity NPC121984
0.8642 High Similarity NPC170394
0.8636 High Similarity NPC474736
0.8625 High Similarity NPC74995
0.8621 High Similarity NPC476437
0.8621 High Similarity NPC48010
0.8621 High Similarity NPC476369
0.8605 High Similarity NPC471791
0.8605 High Similarity NPC471793
0.8588 High Similarity NPC470955
0.8588 High Similarity NPC194417
0.8571 High Similarity NPC214043
0.8571 High Similarity NPC227132
0.8571 High Similarity NPC85774
0.8556 High Similarity NPC471463
0.8554 High Similarity NPC103486
0.8554 High Similarity NPC93590
0.8539 High Similarity NPC476415
0.8539 High Similarity NPC8993
0.8537 High Similarity NPC472478
0.8537 High Similarity NPC306095
0.8537 High Similarity NPC476809
0.8523 High Similarity NPC473998
0.8519 High Similarity NPC239098
0.8519 High Similarity NPC297996
0.8506 High Similarity NPC123912
0.8506 High Similarity NPC2983
0.8506 High Similarity NPC472983
0.8506 High Similarity NPC184663
0.85 High Similarity NPC470525
0.8488 Intermediate Similarity NPC93778
0.8471 Intermediate Similarity NPC470574
0.8471 Intermediate Similarity NPC474083
0.8452 Intermediate Similarity NPC105173
0.8452 Intermediate Similarity NPC307258
0.8444 Intermediate Similarity NPC271195
0.8444 Intermediate Similarity NPC259286
0.8434 Intermediate Similarity NPC473217
0.8434 Intermediate Similarity NPC278459
0.8434 Intermediate Similarity NPC6663
0.8434 Intermediate Similarity NPC116797
0.8434 Intermediate Similarity NPC3915
0.8427 Intermediate Similarity NPC69454
0.8427 Intermediate Similarity NPC472930
0.8427 Intermediate Similarity NPC474807
0.8427 Intermediate Similarity NPC109305
0.8415 Intermediate Similarity NPC152061
0.8395 Intermediate Similarity NPC266193
0.8395 Intermediate Similarity NPC257666
0.8395 Intermediate Similarity NPC97377
0.8395 Intermediate Similarity NPC165711
0.8391 Intermediate Similarity NPC104560
0.8391 Intermediate Similarity NPC48107
0.8391 Intermediate Similarity NPC158778
0.8372 Intermediate Similarity NPC145879
0.8372 Intermediate Similarity NPC474732
0.8372 Intermediate Similarity NPC31564
0.8372 Intermediate Similarity NPC327115
0.8372 Intermediate Similarity NPC469994
0.8372 Intermediate Similarity NPC474733
0.8372 Intermediate Similarity NPC322159
0.8372 Intermediate Similarity NPC474778
0.8354 Intermediate Similarity NPC247586
0.8353 Intermediate Similarity NPC58841
0.8353 Intermediate Similarity NPC473246
0.8353 Intermediate Similarity NPC329043
0.8353 Intermediate Similarity NPC237712
0.8353 Intermediate Similarity NPC161423
0.8353 Intermediate Similarity NPC227064
0.8353 Intermediate Similarity NPC321187
0.8352 Intermediate Similarity NPC249954
0.8333 Intermediate Similarity NPC302661
0.8333 Intermediate Similarity NPC238991
0.8333 Intermediate Similarity NPC299100
0.8333 Intermediate Similarity NPC212083
0.8333 Intermediate Similarity NPC48362
0.8333 Intermediate Similarity NPC310989
0.8315 Intermediate Similarity NPC63748
0.8313 Intermediate Similarity NPC148685
0.8313 Intermediate Similarity NPC104120
0.8313 Intermediate Similarity NPC157895
0.8313 Intermediate Similarity NPC472301
0.8313 Intermediate Similarity NPC172013
0.8313 Intermediate Similarity NPC45495
0.8298 Intermediate Similarity NPC87351
0.8295 Intermediate Similarity NPC477973
0.8295 Intermediate Similarity NPC477943
0.8295 Intermediate Similarity NPC262043
0.8295 Intermediate Similarity NPC186688
0.8295 Intermediate Similarity NPC472475
0.8295 Intermediate Similarity NPC281524
0.8295 Intermediate Similarity NPC472477
0.8293 Intermediate Similarity NPC198240
0.8276 Intermediate Similarity NPC58063
0.8276 Intermediate Similarity NPC471792
0.8276 Intermediate Similarity NPC475740
0.8276 Intermediate Similarity NPC136948
0.8276 Intermediate Similarity NPC287079
0.8272 Intermediate Similarity NPC472305
0.8261 Intermediate Similarity NPC170131
0.8261 Intermediate Similarity NPC253826
0.8256 Intermediate Similarity NPC255174
0.825 Intermediate Similarity NPC215050
0.8242 Intermediate Similarity NPC476174
0.8242 Intermediate Similarity NPC180950
0.8242 Intermediate Similarity NPC472932
0.8235 Intermediate Similarity NPC297398
0.8235 Intermediate Similarity NPC64600
0.8235 Intermediate Similarity NPC102197
0.8235 Intermediate Similarity NPC49019
0.8214 Intermediate Similarity NPC471898
0.8214 Intermediate Similarity NPC90055
0.8214 Intermediate Similarity NPC14151
0.8211 Intermediate Similarity NPC311612
0.8202 Intermediate Similarity NPC320026
0.8202 Intermediate Similarity NPC85173
0.8202 Intermediate Similarity NPC230332
0.8202 Intermediate Similarity NPC134321
0.8193 Intermediate Similarity NPC7232
0.8193 Intermediate Similarity NPC19900
0.8193 Intermediate Similarity NPC472490
0.8193 Intermediate Similarity NPC476177
0.8193 Intermediate Similarity NPC474113
0.8193 Intermediate Similarity NPC281138
0.8182 Intermediate Similarity NPC206060
0.8182 Intermediate Similarity NPC472870
0.8182 Intermediate Similarity NPC328539
0.8182 Intermediate Similarity NPC472802
0.8182 Intermediate Similarity NPC72397
0.8182 Intermediate Similarity NPC474925
0.8182 Intermediate Similarity NPC470524
0.8172 Intermediate Similarity NPC478056
0.8172 Intermediate Similarity NPC197386
0.8172 Intermediate Similarity NPC103051
0.8171 Intermediate Similarity NPC197659
0.8171 Intermediate Similarity NPC325946
0.8171 Intermediate Similarity NPC34110
0.8171 Intermediate Similarity NPC61952
0.8171 Intermediate Similarity NPC203403
0.8161 Intermediate Similarity NPC94666
0.8161 Intermediate Similarity NPC158393
0.8161 Intermediate Similarity NPC82979
0.8161 Intermediate Similarity NPC472869
0.8161 Intermediate Similarity NPC473168
0.8152 Intermediate Similarity NPC29152
0.8152 Intermediate Similarity NPC472941
0.8152 Intermediate Similarity NPC456
0.8148 Intermediate Similarity NPC114236
0.814 Intermediate Similarity NPC472265
0.814 Intermediate Similarity NPC59453
0.814 Intermediate Similarity NPC40687
0.814 Intermediate Similarity NPC82902
0.814 Intermediate Similarity NPC180834
0.814 Intermediate Similarity NPC251170
0.814 Intermediate Similarity NPC221758
0.8132 Intermediate Similarity NPC474882
0.8132 Intermediate Similarity NPC470958
0.8132 Intermediate Similarity NPC473162
0.8132 Intermediate Similarity NPC470957
0.8132 Intermediate Similarity NPC473172
0.8132 Intermediate Similarity NPC471207
0.8125 Intermediate Similarity NPC186042
0.8118 Intermediate Similarity NPC158411
0.8118 Intermediate Similarity NPC38796
0.8118 Intermediate Similarity NPC151519
0.8118 Intermediate Similarity NPC193347
0.8111 Intermediate Similarity NPC233116
0.8111 Intermediate Similarity NPC116726
0.8111 Intermediate Similarity NPC272746
0.8111 Intermediate Similarity NPC230064
0.8105 Intermediate Similarity NPC477915
0.8105 Intermediate Similarity NPC473424
0.8095 Intermediate Similarity NPC271104
0.8095 Intermediate Similarity NPC469637
0.8095 Intermediate Similarity NPC471514
0.8095 Intermediate Similarity NPC108955

  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 NPC476412 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
0.8372 Intermediate Similarity NPD4623 Approved
0.8372 Intermediate Similarity NPD4519 Discontinued
0.8353 Intermediate Similarity NPD3666 Approved
0.8353 Intermediate Similarity NPD3133 Approved
0.8353 Intermediate Similarity NPD3665 Phase 1
0.8315 Intermediate Similarity NPD6079 Approved
0.8313 Intermediate Similarity NPD4695 Discontinued
0.8295 Intermediate Similarity NPD5328 Approved
0.8161 Intermediate Similarity NPD3618 Phase 1
0.814 Intermediate Similarity NPD4786 Approved
0.8118 Intermediate Similarity NPD4221 Approved
0.8118 Intermediate Similarity NPD3667 Approved
0.8118 Intermediate Similarity NPD4223 Phase 3
0.809 Intermediate Similarity NPD4753 Phase 2
0.8046 Intermediate Similarity NPD5329 Approved
0.7955 Intermediate Similarity NPD5279 Phase 3
0.7931 Intermediate Similarity NPD4197 Approved
0.7917 Intermediate Similarity NPD5211 Phase 2
0.7912 Intermediate Similarity NPD7515 Phase 2
0.7849 Intermediate Similarity NPD5210 Approved
0.7849 Intermediate Similarity NPD4629 Approved
0.7826 Intermediate Similarity NPD4202 Approved
0.7816 Intermediate Similarity NPD4788 Approved
0.7766 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD5222 Approved
0.7766 Intermediate Similarity NPD5221 Approved
0.7755 Intermediate Similarity NPD5141 Approved
0.7753 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD4690 Approved
0.7753 Intermediate Similarity NPD5205 Approved
0.7753 Intermediate Similarity NPD4693 Phase 3
0.7753 Intermediate Similarity NPD4138 Approved
0.7753 Intermediate Similarity NPD4689 Approved
0.7753 Intermediate Similarity NPD4688 Approved
0.7753 Intermediate Similarity NPD5690 Phase 2
0.7708 Intermediate Similarity NPD5285 Approved
0.7708 Intermediate Similarity NPD5286 Approved
0.7708 Intermediate Similarity NPD4696 Approved
0.7684 Intermediate Similarity NPD6084 Phase 2
0.7684 Intermediate Similarity NPD6083 Phase 2
0.7684 Intermediate Similarity NPD4755 Approved
0.7684 Intermediate Similarity NPD5173 Approved
0.7647 Intermediate Similarity NPD3617 Approved
0.7629 Intermediate Similarity NPD5223 Approved
0.7595 Intermediate Similarity NPD7331 Phase 2
0.7579 Intermediate Similarity NPD4697 Phase 3
0.7558 Intermediate Similarity NPD4195 Approved
0.7556 Intermediate Similarity NPD6409 Approved
0.7556 Intermediate Similarity NPD5280 Approved
0.7556 Intermediate Similarity NPD6684 Approved
0.7556 Intermediate Similarity NPD7146 Approved
0.7556 Intermediate Similarity NPD7521 Approved
0.7556 Intermediate Similarity NPD7334 Approved
0.7556 Intermediate Similarity NPD4694 Approved
0.7556 Intermediate Similarity NPD5330 Approved
0.7553 Intermediate Similarity NPD7748 Approved
0.7551 Intermediate Similarity NPD4633 Approved
0.7551 Intermediate Similarity NPD5225 Approved
0.7551 Intermediate Similarity NPD5226 Approved
0.7551 Intermediate Similarity NPD5224 Approved
0.7526 Intermediate Similarity NPD4700 Approved
0.75 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD5174 Approved
0.7475 Intermediate Similarity NPD5175 Approved
0.7473 Intermediate Similarity NPD3573 Approved
0.7468 Intermediate Similarity NPD7341 Phase 2
0.7444 Intermediate Similarity NPD1696 Phase 3
0.7439 Intermediate Similarity NPD4691 Approved
0.7391 Intermediate Similarity NPD5737 Approved
0.7391 Intermediate Similarity NPD6903 Approved
0.7391 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6672 Approved
0.7353 Intermediate Similarity NPD6899 Approved
0.7353 Intermediate Similarity NPD6881 Approved
0.7333 Intermediate Similarity NPD3668 Phase 3
0.7327 Intermediate Similarity NPD6402 Approved
0.7327 Intermediate Similarity NPD7128 Approved
0.7327 Intermediate Similarity NPD5739 Approved
0.7327 Intermediate Similarity NPD6675 Approved
0.732 Intermediate Similarity NPD7902 Approved
0.7317 Intermediate Similarity NPD4137 Phase 3
0.7312 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD4754 Approved
0.7292 Intermediate Similarity NPD5695 Phase 3
0.7263 Intermediate Similarity NPD6399 Phase 3
0.7255 Intermediate Similarity NPD5697 Approved
0.7245 Intermediate Similarity NPD5696 Approved
0.7234 Intermediate Similarity NPD4096 Approved
0.7229 Intermediate Similarity NPD4747 Approved
0.7216 Intermediate Similarity NPD7614 Phase 1
0.7212 Intermediate Similarity NPD7102 Approved
0.7212 Intermediate Similarity NPD6883 Approved
0.7212 Intermediate Similarity NPD7290 Approved
0.7184 Intermediate Similarity NPD7320 Approved
0.7184 Intermediate Similarity NPD6011 Approved
0.7184 Intermediate Similarity NPD4729 Approved
0.7184 Intermediate Similarity NPD4730 Approved
0.7184 Intermediate Similarity NPD5128 Approved
0.7176 Intermediate Similarity NPD4058 Approved
0.7172 Intermediate Similarity NPD7639 Approved
0.7172 Intermediate Similarity NPD7640 Approved
0.7158 Intermediate Similarity NPD5281 Approved
0.7158 Intermediate Similarity NPD5284 Approved
0.7157 Intermediate Similarity NPD4767 Approved
0.7157 Intermediate Similarity NPD4768 Approved
0.7143 Intermediate Similarity NPD8130 Phase 1
0.7143 Intermediate Similarity NPD6869 Approved
0.7143 Intermediate Similarity NPD6617 Approved
0.7143 Intermediate Similarity NPD6847 Approved
0.7143 Intermediate Similarity NPD6649 Approved
0.7143 Intermediate Similarity NPD6650 Approved
0.713 Intermediate Similarity NPD7115 Discovery
0.7128 Intermediate Similarity NPD6904 Approved
0.7128 Intermediate Similarity NPD6673 Approved
0.7128 Intermediate Similarity NPD6080 Approved
0.7115 Intermediate Similarity NPD6013 Approved
0.7115 Intermediate Similarity NPD6373 Approved
0.7115 Intermediate Similarity NPD6372 Approved
0.7115 Intermediate Similarity NPD6014 Approved
0.7115 Intermediate Similarity NPD6012 Approved
0.7093 Intermediate Similarity NPD7339 Approved
0.7093 Intermediate Similarity NPD6942 Approved
0.7087 Intermediate Similarity NPD5701 Approved
0.7075 Intermediate Similarity NPD6882 Approved
0.7075 Intermediate Similarity NPD8297 Approved
0.7071 Intermediate Similarity NPD7638 Approved
0.7048 Intermediate Similarity NPD5251 Approved
0.7048 Intermediate Similarity NPD5247 Approved
0.7048 Intermediate Similarity NPD5248 Approved
0.7048 Intermediate Similarity NPD5135 Approved
0.7048 Intermediate Similarity NPD5169 Approved
0.7048 Intermediate Similarity NPD5249 Phase 3
0.7048 Intermediate Similarity NPD5250 Approved
0.7048 Intermediate Similarity NPD4634 Approved
0.7048 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD4518 Approved
0.7021 Intermediate Similarity NPD5208 Approved
0.7019 Intermediate Similarity NPD6686 Approved
0.7019 Intermediate Similarity NPD5168 Approved
0.7011 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD7900 Approved
0.701 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4692 Approved
0.7 Intermediate Similarity NPD6404 Discontinued
0.7 Intermediate Similarity NPD4139 Approved
0.6989 Remote Similarity NPD6098 Approved
0.6981 Remote Similarity NPD5127 Approved
0.6981 Remote Similarity NPD5217 Approved
0.6981 Remote Similarity NPD5216 Approved
0.6981 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5215 Approved
0.6979 Remote Similarity NPD5693 Phase 1
0.6979 Remote Similarity NPD6411 Approved
0.6977 Remote Similarity NPD6926 Approved
0.6977 Remote Similarity NPD5733 Approved
0.6977 Remote Similarity NPD6924 Approved
0.6966 Remote Similarity NPD7645 Phase 2
0.6941 Remote Similarity NPD4243 Approved
0.6941 Remote Similarity NPD5276 Approved
0.6939 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6412 Phase 2
0.6915 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6907 Remote Similarity NPD5779 Approved
0.6907 Remote Similarity NPD5133 Approved
0.6907 Remote Similarity NPD5778 Approved
0.69 Remote Similarity NPD4225 Approved
0.6897 Remote Similarity NPD8264 Approved
0.6889 Remote Similarity NPD7525 Registered
0.6889 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6889 Remote Similarity NPD6930 Phase 2
0.6889 Remote Similarity NPD6931 Approved
0.6882 Remote Similarity NPD1694 Approved
0.6882 Remote Similarity NPD5363 Approved
0.6882 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5785 Approved
0.6869 Remote Similarity NPD7732 Phase 3
0.6863 Remote Similarity NPD5091 Approved
0.6854 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6852 Remote Similarity NPD4632 Approved
0.6818 Remote Similarity NPD6933 Approved
0.6804 Remote Similarity NPD6050 Approved
0.6789 Remote Similarity NPD5167 Approved
0.6786 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4687 Approved
0.6782 Remote Similarity NPD4784 Approved
0.6782 Remote Similarity NPD4785 Approved
0.6778 Remote Similarity NPD6929 Approved
0.6771 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6771 Remote Similarity NPD6101 Approved
0.6757 Remote Similarity NPD6335 Approved
0.6727 Remote Similarity NPD6868 Approved
0.6727 Remote Similarity NPD6274 Approved
0.6703 Remote Similarity NPD7514 Phase 3
0.6703 Remote Similarity NPD7332 Phase 2
0.6701 Remote Similarity NPD5207 Approved
0.6701 Remote Similarity NPD5692 Phase 3
0.6696 Remote Similarity NPD7100 Approved
0.6696 Remote Similarity NPD7101 Approved
0.6667 Remote Similarity NPD6695 Phase 3

  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