Structure

Physi-Chem Properties

Molecular Weight:  380.26
Volume:  407.997
LogP:  3.603
LogD:  2.409
LogS:  -3.888
# Rotatable Bonds:  7
TPSA:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.529
Synthetic Accessibility Score:  4.432
Fsp3:  0.818
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.215
MDCK Permeability:  2.4611228582216427e-05
Pgp-inhibitor:  0.137
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.194
30% Bioavailability (F30%):  0.355

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  89.20193481445312%
Volume Distribution (VD):  0.479
Pgp-substrate:  11.114497184753418%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.132
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.784
CYP2C9-inhibitor:  0.066
CYP2C9-substrate:  0.729
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.097
CYP3A4-inhibitor:  0.108
CYP3A4-substrate:  0.101

ADMET: Excretion

Clearance (CL):  2.204
Half-life (T1/2):  0.874

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.057
Drug-inuced Liver Injury (DILI):  0.144
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.016
Maximum Recommended Daily Dose:  0.021
Skin Sensitization:  0.834
Carcinogencity:  0.108
Eye Corrosion:  0.849
Eye Irritation:  0.904
Respiratory Toxicity:  0.531

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

  Natural Product: NPC476927

Natural Product ID:  NPC476927
Common Name*:   (13E)-8-Hydroxy-18-acetoxylabda-13-ene-15-oic acid
IUPAC Name:   (E)-5-[(1R,2R,4aR,5R,8aS)-5-(acetyloxymethyl)-2-hydroxy-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
Synonyms:  
Standard InCHIKey:  ISGZIAHLYCQZFM-DJKOWVEXSA-N
Standard InCHI:  InChI=1S/C22H36O5/c1-15(13-19(24)25)7-8-18-21(4)11-6-10-20(3,14-27-16(2)23)17(21)9-12-22(18,5)26/h13,17-18,26H,6-12,14H2,1-5H3,(H,24,25)/b15-13+/t17-,18+,20-,21-,22+/m0/s1
SMILES:  C/C(=C\C(=O)O)/CC[C@@H]1[C@]2(CCC[C@@]([C@@H]2CC[C@@]1(C)O)(C)COC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   24899924
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] 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
NPO25356 Crassocephalum mannii Species Asteraceae Eukaryota aerial parts n.a. n.a. PMID[18473477]
NPO25356 Crassocephalum mannii Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[18473477]
NPO25356 Crassocephalum mannii Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[18473477]
NPO25356 Crassocephalum mannii Species Asteraceae 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
NPT324 Individual Protein Cyclooxygenase-1 Ovis aries Inhibition = 2 % PMID[18473477]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens Inhibition = 25 % PMID[18473477]

☑ 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 NPC476927 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
0.9615 High Similarity NPC2524
0.9487 High Similarity NPC170303
0.9375 High Similarity NPC306951
0.9367 High Similarity NPC256112
0.9221 High Similarity NPC132542
0.9146 High Similarity NPC475069
0.9146 High Similarity NPC175145
0.9114 High Similarity NPC281880
0.9 High Similarity NPC159148
0.8941 High Similarity NPC78973
0.8837 High Similarity NPC329842
0.8824 High Similarity NPC170633
0.881 High Similarity NPC166857
0.878 High Similarity NPC79945
0.8736 High Similarity NPC7349
0.8736 High Similarity NPC38232
0.869 High Similarity NPC131813
0.8675 High Similarity NPC102048
0.8636 High Similarity NPC105490
0.8605 High Similarity NPC82876
0.859 High Similarity NPC201048
0.859 High Similarity NPC476366
0.8571 High Similarity NPC474013
0.8571 High Similarity NPC109528
0.8539 High Similarity NPC472441
0.8539 High Similarity NPC276110
0.8523 High Similarity NPC53555
0.8488 Intermediate Similarity NPC104560
0.8488 Intermediate Similarity NPC291665
0.8488 Intermediate Similarity NPC93411
0.8427 Intermediate Similarity NPC279410
0.8427 Intermediate Similarity NPC119562
0.8409 Intermediate Similarity NPC472811
0.8391 Intermediate Similarity NPC472240
0.8391 Intermediate Similarity NPC262858
0.8391 Intermediate Similarity NPC314727
0.8391 Intermediate Similarity NPC16265
0.8375 Intermediate Similarity NPC470749
0.8372 Intermediate Similarity NPC131329
0.8372 Intermediate Similarity NPC245004
0.837 Intermediate Similarity NPC324841
0.837 Intermediate Similarity NPC38855
0.8353 Intermediate Similarity NPC164424
0.8353 Intermediate Similarity NPC35933
0.8333 Intermediate Similarity NPC311070
0.8315 Intermediate Similarity NPC472812
0.8315 Intermediate Similarity NPC476304
0.8315 Intermediate Similarity NPC472871
0.8313 Intermediate Similarity NPC142163
0.8293 Intermediate Similarity NPC242767
0.8276 Intermediate Similarity NPC472870
0.8276 Intermediate Similarity NPC48107
0.8276 Intermediate Similarity NPC106332
0.8272 Intermediate Similarity NPC470758
0.8272 Intermediate Similarity NPC470711
0.8272 Intermediate Similarity NPC283619
0.8261 Intermediate Similarity NPC278673
0.8261 Intermediate Similarity NPC218107
0.8261 Intermediate Similarity NPC478056
0.8261 Intermediate Similarity NPC325229
0.8261 Intermediate Similarity NPC275086
0.8256 Intermediate Similarity NPC471219
0.8256 Intermediate Similarity NPC474970
0.8256 Intermediate Similarity NPC73038
0.825 Intermediate Similarity NPC32832
0.8235 Intermediate Similarity NPC302360
0.8235 Intermediate Similarity NPC96055
0.8222 Intermediate Similarity NPC57117
0.8222 Intermediate Similarity NPC476186
0.8214 Intermediate Similarity NPC155521
0.8214 Intermediate Similarity NPC471218
0.8202 Intermediate Similarity NPC110923
0.8202 Intermediate Similarity NPC72845
0.8202 Intermediate Similarity NPC473675
0.8202 Intermediate Similarity NPC74296
0.8202 Intermediate Similarity NPC177641
0.8193 Intermediate Similarity NPC469802
0.8191 Intermediate Similarity NPC475038
0.8191 Intermediate Similarity NPC109195
0.8182 Intermediate Similarity NPC246028
0.8182 Intermediate Similarity NPC20946
0.8182 Intermediate Similarity NPC50488
0.8182 Intermediate Similarity NPC474396
0.8182 Intermediate Similarity NPC36668
0.8182 Intermediate Similarity NPC118011
0.8182 Intermediate Similarity NPC146554
0.8172 Intermediate Similarity NPC251680
0.8172 Intermediate Similarity NPC266955
0.8172 Intermediate Similarity NPC471413
0.8152 Intermediate Similarity NPC51499
0.8152 Intermediate Similarity NPC141401
0.8152 Intermediate Similarity NPC170131
0.8152 Intermediate Similarity NPC99726
0.814 Intermediate Similarity NPC30984
0.814 Intermediate Similarity NPC191965
0.8125 Intermediate Similarity NPC71152
0.8118 Intermediate Similarity NPC57370
0.8118 Intermediate Similarity NPC52108
0.8118 Intermediate Similarity NPC42476
0.8118 Intermediate Similarity NPC473592
0.8118 Intermediate Similarity NPC23748
0.8118 Intermediate Similarity NPC49208
0.8118 Intermediate Similarity NPC474789
0.8111 Intermediate Similarity NPC214697
0.8111 Intermediate Similarity NPC205034
0.8111 Intermediate Similarity NPC152778
0.8111 Intermediate Similarity NPC139692
0.8111 Intermediate Similarity NPC476416
0.8111 Intermediate Similarity NPC472303
0.8111 Intermediate Similarity NPC162615
0.8105 Intermediate Similarity NPC72151
0.8105 Intermediate Similarity NPC478057
0.8101 Intermediate Similarity NPC167706
0.8095 Intermediate Similarity NPC40228
0.8095 Intermediate Similarity NPC229584
0.8095 Intermediate Similarity NPC14203
0.8095 Intermediate Similarity NPC327002
0.8095 Intermediate Similarity NPC25554
0.809 Intermediate Similarity NPC182136
0.809 Intermediate Similarity NPC232202
0.809 Intermediate Similarity NPC280149
0.809 Intermediate Similarity NPC221111
0.809 Intermediate Similarity NPC310479
0.809 Intermediate Similarity NPC472866
0.8085 Intermediate Similarity NPC471412
0.8085 Intermediate Similarity NPC268829
0.8085 Intermediate Similarity NPC295110
0.8085 Intermediate Similarity NPC25177
0.8085 Intermediate Similarity NPC222875
0.8085 Intermediate Similarity NPC115899
0.8085 Intermediate Similarity NPC11974
0.8085 Intermediate Similarity NPC118174
0.8085 Intermediate Similarity NPC247701
0.8072 Intermediate Similarity NPC476438
0.8072 Intermediate Similarity NPC192999
0.8072 Intermediate Similarity NPC170394
0.8072 Intermediate Similarity NPC100906
0.8068 Intermediate Similarity NPC472810
0.8068 Intermediate Similarity NPC472809
0.8068 Intermediate Similarity NPC229612
0.8068 Intermediate Similarity NPC7280
0.8065 Intermediate Similarity NPC316598
0.8049 Intermediate Similarity NPC61952
0.8046 Intermediate Similarity NPC325594
0.8046 Intermediate Similarity NPC137306
0.8046 Intermediate Similarity NPC473226
0.8046 Intermediate Similarity NPC84121
0.8046 Intermediate Similarity NPC472869
0.8046 Intermediate Similarity NPC329692
0.8046 Intermediate Similarity NPC322159
0.8043 Intermediate Similarity NPC234993
0.8043 Intermediate Similarity NPC473153
0.8043 Intermediate Similarity NPC16967
0.8043 Intermediate Similarity NPC301534
0.8043 Intermediate Similarity NPC250757
0.8043 Intermediate Similarity NPC54248
0.8043 Intermediate Similarity NPC276103
0.8043 Intermediate Similarity NPC29952
0.8043 Intermediate Similarity NPC190713
0.8043 Intermediate Similarity NPC195366
0.8043 Intermediate Similarity NPC114743
0.8043 Intermediate Similarity NPC242848
0.8043 Intermediate Similarity NPC134072
0.8023 Intermediate Similarity NPC32223
0.8023 Intermediate Similarity NPC471302
0.8022 Intermediate Similarity NPC74751
0.8022 Intermediate Similarity NPC201725
0.8022 Intermediate Similarity NPC474922
0.8022 Intermediate Similarity NPC470255
0.8022 Intermediate Similarity NPC140277
0.8022 Intermediate Similarity NPC469697
0.8 Intermediate Similarity NPC476081
0.8 Intermediate Similarity NPC472815
0.8 Intermediate Similarity NPC162973
0.8 Intermediate Similarity NPC212948
0.8 Intermediate Similarity NPC286786
0.8 Intermediate Similarity NPC470113
0.8 Intermediate Similarity NPC289479
0.8 Intermediate Similarity NPC476417
0.8 Intermediate Similarity NPC320447
0.7979 Intermediate Similarity NPC16601
0.7979 Intermediate Similarity NPC474190
0.7979 Intermediate Similarity NPC470074
0.7979 Intermediate Similarity NPC472826
0.7979 Intermediate Similarity NPC471041
0.7978 Intermediate Similarity NPC470734
0.7978 Intermediate Similarity NPC174342
0.7976 Intermediate Similarity NPC10636
0.7976 Intermediate Similarity NPC269791
0.7976 Intermediate Similarity NPC206735
0.7957 Intermediate Similarity NPC231751
0.7957 Intermediate Similarity NPC473456
0.7957 Intermediate Similarity NPC210337
0.7957 Intermediate Similarity NPC253826
0.7957 Intermediate Similarity NPC73911
0.7955 Intermediate Similarity NPC128644
0.7955 Intermediate Similarity NPC264546
0.7952 Intermediate Similarity NPC321514
0.7952 Intermediate Similarity NPC198240
0.7952 Intermediate Similarity NPC239098

  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 NPC476927 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
0.8172 Intermediate Similarity NPD7640 Approved
0.8172 Intermediate Similarity NPD7639 Approved
0.8065 Intermediate Similarity NPD7638 Approved
0.8022 Intermediate Similarity NPD7748 Approved
0.7872 Intermediate Similarity NPD4225 Approved
0.7802 Intermediate Similarity NPD7515 Phase 2
0.7766 Intermediate Similarity NPD7902 Approved
0.7586 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD7525 Registered
0.7449 Intermediate Similarity NPD7632 Discontinued
0.7447 Intermediate Similarity NPD7900 Approved
0.7447 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD7645 Phase 2
0.74 Intermediate Similarity NPD5739 Approved
0.74 Intermediate Similarity NPD7128 Approved
0.74 Intermediate Similarity NPD6675 Approved
0.74 Intermediate Similarity NPD6402 Approved
0.7396 Intermediate Similarity NPD6084 Phase 2
0.7396 Intermediate Similarity NPD6083 Phase 2
0.7391 Intermediate Similarity NPD6051 Approved
0.7363 Intermediate Similarity NPD3573 Approved
0.734 Intermediate Similarity NPD6399 Phase 3
0.7283 Intermediate Similarity NPD6672 Approved
0.7283 Intermediate Similarity NPD5737 Approved
0.7255 Intermediate Similarity NPD6899 Approved
0.7255 Intermediate Similarity NPD6881 Approved
0.7255 Intermediate Similarity NPD7320 Approved
0.7253 Intermediate Similarity NPD6409 Approved
0.7253 Intermediate Similarity NPD6684 Approved
0.7253 Intermediate Similarity NPD5330 Approved
0.7253 Intermediate Similarity NPD7146 Approved
0.7253 Intermediate Similarity NPD7334 Approved
0.7253 Intermediate Similarity NPD3618 Phase 1
0.7253 Intermediate Similarity NPD7521 Approved
0.7204 Intermediate Similarity NPD5328 Approved
0.7196 Intermediate Similarity NPD7115 Discovery
0.7188 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD5695 Phase 3
0.7184 Intermediate Similarity NPD6372 Approved
0.7184 Intermediate Similarity NPD6373 Approved
0.7172 Intermediate Similarity NPD5344 Discontinued
0.7157 Intermediate Similarity NPD5701 Approved
0.7157 Intermediate Similarity NPD5697 Approved
0.7143 Intermediate Similarity NPD5696 Approved
0.7115 Intermediate Similarity NPD7290 Approved
0.7115 Intermediate Similarity NPD6883 Approved
0.7115 Intermediate Similarity NPD7102 Approved
0.7111 Intermediate Similarity NPD6695 Phase 3
0.7097 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6903 Approved
0.7087 Intermediate Similarity NPD6011 Approved
0.7071 Intermediate Similarity NPD6648 Approved
0.7065 Intermediate Similarity NPD4623 Approved
0.7065 Intermediate Similarity NPD4519 Discontinued
0.7053 Intermediate Similarity NPD6079 Approved
0.7053 Intermediate Similarity NPD8035 Phase 2
0.7053 Intermediate Similarity NPD7637 Suspended
0.7053 Intermediate Similarity NPD8034 Phase 2
0.7048 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6869 Approved
0.7048 Intermediate Similarity NPD6650 Approved
0.7048 Intermediate Similarity NPD6847 Approved
0.7048 Intermediate Similarity NPD6649 Approved
0.7048 Intermediate Similarity NPD8130 Phase 1
0.7048 Intermediate Similarity NPD6617 Approved
0.7045 Intermediate Similarity NPD4195 Approved
0.7033 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6673 Approved
0.7021 Intermediate Similarity NPD6080 Approved
0.7021 Intermediate Similarity NPD6904 Approved
0.7019 Intermediate Similarity NPD6012 Approved
0.7019 Intermediate Similarity NPD6013 Approved
0.7019 Intermediate Similarity NPD6014 Approved
0.6981 Remote Similarity NPD8297 Approved
0.6981 Remote Similarity NPD6882 Approved
0.6979 Remote Similarity NPD4202 Approved
0.6977 Remote Similarity NPD7339 Approved
0.6977 Remote Similarity NPD6942 Approved
0.6977 Remote Similarity NPD8264 Approved
0.6972 Remote Similarity NPD7328 Approved
0.6972 Remote Similarity NPD7327 Approved
0.6957 Remote Similarity NPD1694 Approved
0.6957 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6931 Remote Similarity NPD5211 Phase 2
0.6909 Remote Similarity NPD7516 Approved
0.6897 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6882 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5693 Phase 1
0.6869 Remote Similarity NPD4755 Approved
0.686 Remote Similarity NPD6926 Approved
0.686 Remote Similarity NPD6924 Approved
0.6857 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6848 Remote Similarity NPD3133 Approved
0.6848 Remote Similarity NPD4786 Approved
0.6848 Remote Similarity NPD3666 Approved
0.6848 Remote Similarity NPD3665 Phase 1
0.6847 Remote Similarity NPD8294 Approved
0.6847 Remote Similarity NPD8377 Approved
0.6842 Remote Similarity NPD4753 Phase 2
0.6842 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6824 Remote Similarity NPD4243 Approved
0.6813 Remote Similarity NPD3667 Approved
0.6813 Remote Similarity NPD4223 Phase 3
0.6813 Remote Similarity NPD4221 Approved
0.6809 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7750 Discontinued
0.6809 Remote Similarity NPD7524 Approved
0.6804 Remote Similarity NPD5778 Approved
0.6804 Remote Similarity NPD5779 Approved
0.6796 Remote Similarity NPD5141 Approved
0.6792 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8296 Approved
0.6786 Remote Similarity NPD8380 Approved
0.6786 Remote Similarity NPD8379 Approved
0.6786 Remote Similarity NPD8378 Approved
0.6786 Remote Similarity NPD8335 Approved
0.6786 Remote Similarity NPD8033 Approved
0.6778 Remote Similarity NPD6931 Approved
0.6778 Remote Similarity NPD6930 Phase 2
0.6778 Remote Similarity NPD4695 Discontinued
0.6774 Remote Similarity NPD5329 Approved
0.6768 Remote Similarity NPD4697 Phase 3
0.6768 Remote Similarity NPD5221 Approved
0.6768 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6768 Remote Similarity NPD5222 Approved
0.6762 Remote Similarity NPD6686 Approved
0.6742 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6737 Remote Similarity NPD5208 Approved
0.6735 Remote Similarity NPD6001 Approved
0.6733 Remote Similarity NPD5285 Approved
0.6733 Remote Similarity NPD4700 Approved
0.6733 Remote Similarity NPD5286 Approved
0.6733 Remote Similarity NPD4696 Approved
0.6731 Remote Similarity NPD6008 Approved
0.6707 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6933 Approved
0.6702 Remote Similarity NPD6098 Approved
0.6701 Remote Similarity NPD6411 Approved
0.6701 Remote Similarity NPD5284 Approved
0.6701 Remote Similarity NPD5281 Approved
0.6701 Remote Similarity NPD6050 Approved
0.67 Remote Similarity NPD5173 Approved
0.6667 Remote Similarity NPD4785 Approved
0.6667 Remote Similarity NPD5223 Approved
0.6667 Remote Similarity NPD6335 Approved
0.6667 Remote Similarity NPD4197 Approved
0.6667 Remote Similarity NPD4784 Approved
0.6667 Remote Similarity NPD6929 Approved
0.6637 Remote Similarity NPD7503 Approved
0.6636 Remote Similarity NPD6868 Approved
0.6636 Remote Similarity NPD6274 Approved
0.6607 Remote Similarity NPD7101 Approved
0.6607 Remote Similarity NPD7100 Approved
0.6606 Remote Similarity NPD4632 Approved
0.6602 Remote Similarity NPD5225 Approved
0.6602 Remote Similarity NPD5224 Approved
0.6602 Remote Similarity NPD5226 Approved
0.6602 Remote Similarity NPD4633 Approved
0.6598 Remote Similarity NPD5692 Phase 3
0.6596 Remote Similarity NPD1696 Phase 3
0.6593 Remote Similarity NPD7509 Discontinued
0.6593 Remote Similarity NPD7514 Phase 3
0.6593 Remote Similarity NPD7332 Phase 2
0.6577 Remote Similarity NPD6317 Approved
0.6556 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7507 Approved
0.6543 Remote Similarity NPD4192 Approved
0.6543 Remote Similarity NPD4191 Approved
0.6543 Remote Similarity NPD368 Approved
0.6543 Remote Similarity NPD4193 Approved
0.6543 Remote Similarity NPD4194 Approved
0.6538 Remote Similarity NPD4754 Approved
0.6538 Remote Similarity NPD5174 Approved
0.6538 Remote Similarity NPD5175 Approved
0.6531 Remote Similarity NPD7087 Discontinued
0.6531 Remote Similarity NPD5694 Approved
0.6526 Remote Similarity NPD4138 Approved
0.6526 Remote Similarity NPD4690 Approved
0.6526 Remote Similarity NPD4693 Phase 3
0.6526 Remote Similarity NPD4688 Approved
0.6526 Remote Similarity NPD5205 Approved
0.6526 Remote Similarity NPD4689 Approved
0.6518 Remote Similarity NPD6314 Approved
0.6518 Remote Similarity NPD6313 Approved
0.6509 Remote Similarity NPD5954 Clinical (unspecified phase)
0.65 Remote Similarity NPD5210 Approved
0.65 Remote Similarity NPD4629 Approved
0.6495 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6495 Remote Similarity NPD6101 Approved
0.6491 Remote Similarity NPD6909 Approved
0.6491 Remote Similarity NPD6908 Approved
0.6489 Remote Similarity NPD3668 Phase 3
0.6471 Remote Similarity NPD5290 Discontinued
0.6444 Remote Similarity NPD5776 Phase 2
0.6444 Remote Similarity NPD6925 Approved
0.6437 Remote Similarity NPD7152 Approved
0.6437 Remote Similarity NPD7150 Approved
0.6437 Remote Similarity NPD7151 Approved
0.6436 Remote Similarity NPD7614 Phase 1

  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