Structure

Physi-Chem Properties

Molecular Weight:  248.14
Volume:  260.788
LogP:  2.131
LogD:  1.794
LogS:  -3.213
# Rotatable Bonds:  0
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.406
Synthetic Accessibility Score:  4.464
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.688
MDCK Permeability:  2.1276160623528995e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.068
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.168
Plasma Protein Binding (PPB):  62.50822448730469%
Volume Distribution (VD):  0.931
Pgp-substrate:  38.300376892089844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.112
CYP1A2-substrate:  0.101
CYP2C19-inhibitor:  0.031
CYP2C19-substrate:  0.262
CYP2C9-inhibitor:  0.119
CYP2C9-substrate:  0.208
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.345
CYP3A4-inhibitor:  0.068
CYP3A4-substrate:  0.251

ADMET: Excretion

Clearance (CL):  7.284
Half-life (T1/2):  0.435

ADMET: Toxicity

hERG Blockers:  0.152
Human Hepatotoxicity (H-HT):  0.205
Drug-inuced Liver Injury (DILI):  0.262
AMES Toxicity:  0.328
Rat Oral Acute Toxicity:  0.964
Maximum Recommended Daily Dose:  0.979
Skin Sensitization:  0.6
Carcinogencity:  0.487
Eye Corrosion:  0.156
Eye Irritation:  0.719
Respiratory Toxicity:  0.967

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

  Natural Product: NPC305029

Natural Product ID:  NPC305029
Common Name*:   Asperilin
IUPAC Name:   (3aR,4aS,8R,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
Synonyms:   Asperilin
Standard InCHIKey:  GAUPAOVCTWBVKC-WPLOAARJSA-N
Standard InCHI:  InChI=1S/C15H20O3/c1-8-4-5-13(16)15(3)7-12-10(6-11(8)15)9(2)14(17)18-12/h10-13,16H,1-2,4-7H2,3H3/t10-,11+,12-,13-,15-/m1/s1
SMILES:  O=C1O[C@H]2[C@@H](C1=C)C[C@@H]1[C@](C2)(C)[C@H](O)CCC1=C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL272445
PubChem CID:   257274
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, 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
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27276091]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25152 Telekia speciosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25152 Telekia speciosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21728 Iva asperifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25058 Mayetiola destructor Species Cecidomyiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25152 Telekia speciosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23330 Guatteria dumetorum Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25374 Crotalaria sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21728 Iva asperifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24701 Schizonepeta annua Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24797 Chuquiraga ulicina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24524 Gutierrezia gymnospermoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9124 Inula japonica 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 5942.92 nM PMID[486280]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 11376.27 nM PMID[486280]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 14387.99 nM PMID[486280]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 10764.65 nM PMID[486280]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 5128.61 nM PMID[486280]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 10990.06 nM PMID[486280]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 3111.72 nM PMID[486280]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 4255.98 nM PMID[486280]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 2387.81 nM PMID[486280]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 8147.04 nM PMID[486280]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 17139.57 nM PMID[486280]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 13365.96 nM PMID[486280]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 7244.36 nM PMID[486280]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 6123.5 nM PMID[486280]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 18706.82 nM PMID[486280]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 8375.29 nM PMID[486280]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 3140.51 nM PMID[486280]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 12502.59 nM PMID[486280]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 3443.5 nM PMID[486280]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 6683.44 nM PMID[486280]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 4159.11 nM PMID[486280]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 3491.4 nM PMID[486280]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 2594.18 nM PMID[486280]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 3311.31 nM PMID[486280]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 3459.39 nM PMID[486280]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 7516.23 nM PMID[486280]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 11776.06 nM PMID[486280]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 5272.3 nM PMID[486280]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 11614.49 nM PMID[486280]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 21527.82 nM PMID[486280]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 7533.56 nM PMID[486280]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 3689.78 nM PMID[486280]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 7046.93 nM PMID[486280]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 11297.96 nM PMID[486280]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 15595.53 nM PMID[486280]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 4864.07 nM PMID[486280]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 16143.59 nM PMID[486280]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 2754.23 nM PMID[486280]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 14421.15 nM PMID[486280]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 22284.35 nM PMID[486280]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 6137.62 nM PMID[486280]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 5956.62 nM PMID[486280]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 5584.7 nM PMID[486280]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 14092.89 nM PMID[486280]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 20464.45 nM PMID[486280]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 13614.45 nM PMID[486280]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 6039.49 nM PMID[486280]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 9660.51 nM PMID[486280]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 3689.78 nM PMID[486280]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 3006.08 nM PMID[486280]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 4285.49 nM PMID[486280]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 3597.49 nM PMID[486280]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 7585.78 nM PMID[486280]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 2716.44 nM PMID[486280]
NPT20967 CELL-LINE Platelet n.a. IC50 = 57620.0 nM PMID[486279]

☑ 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 NPC305029 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
0.9877 High Similarity NPC85698
0.9756 High Similarity NPC181103
0.9524 High Similarity NPC116620
0.9398 High Similarity NPC185638
0.9398 High Similarity NPC9231
0.9398 High Similarity NPC477920
0.9383 High Similarity NPC226988
0.931 High Similarity NPC148000
0.931 High Similarity NPC469596
0.931 High Similarity NPC225474
0.931 High Similarity NPC24861
0.9302 High Similarity NPC233345
0.9302 High Similarity NPC186363
0.9286 High Similarity NPC470012
0.9259 High Similarity NPC223330
0.9259 High Similarity NPC209318
0.9205 High Similarity NPC157686
0.9205 High Similarity NPC259042
0.9176 High Similarity NPC277771
0.9101 High Similarity NPC93245
0.9 High Similarity NPC136781
0.9 High Similarity NPC473963
0.8989 High Similarity NPC90014
0.8929 High Similarity NPC97505
0.8889 High Similarity NPC473964
0.8851 High Similarity NPC194642
0.8837 High Similarity NPC175293
0.881 High Similarity NPC194637
0.8804 High Similarity NPC47024
0.8795 High Similarity NPC38642
0.8778 High Similarity NPC183012
0.875 High Similarity NPC475776
0.8721 High Similarity NPC6979
0.8721 High Similarity NPC250981
0.871 High Similarity NPC475958
0.8706 High Similarity NPC219011
0.8706 High Similarity NPC470011
0.8696 High Similarity NPC216478
0.8696 High Similarity NPC473155
0.8696 High Similarity NPC476806
0.8696 High Similarity NPC476807
0.8681 High Similarity NPC284518
0.8681 High Similarity NPC165528
0.8681 High Similarity NPC228766
0.8642 High Similarity NPC92489
0.8588 High Similarity NPC243347
0.8556 High Similarity NPC147272
0.8554 High Similarity NPC263951
0.8539 High Similarity NPC158488
0.8526 High Similarity NPC61442
0.8444 Intermediate Similarity NPC72845
0.8427 Intermediate Similarity NPC474396
0.8427 Intermediate Similarity NPC50488
0.8427 Intermediate Similarity NPC73995
0.8421 Intermediate Similarity NPC164551
0.8404 Intermediate Similarity NPC476303
0.8387 Intermediate Similarity NPC474343
0.8372 Intermediate Similarity NPC470948
0.837 Intermediate Similarity NPC56369
0.8353 Intermediate Similarity NPC475951
0.8352 Intermediate Similarity NPC139692
0.8333 Intermediate Similarity NPC153853
0.8333 Intermediate Similarity NPC152467
0.8333 Intermediate Similarity NPC72842
0.8333 Intermediate Similarity NPC476237
0.8316 Intermediate Similarity NPC242666
0.8316 Intermediate Similarity NPC308824
0.8315 Intermediate Similarity NPC477302
0.8315 Intermediate Similarity NPC136879
0.8315 Intermediate Similarity NPC215831
0.8295 Intermediate Similarity NPC329692
0.828 Intermediate Similarity NPC154526
0.828 Intermediate Similarity NPC472362
0.828 Intermediate Similarity NPC472363
0.8276 Intermediate Similarity NPC130966
0.8265 Intermediate Similarity NPC78966
0.8265 Intermediate Similarity NPC284732
0.8265 Intermediate Similarity NPC110496
0.8261 Intermediate Similarity NPC473434
0.8261 Intermediate Similarity NPC250075
0.8261 Intermediate Similarity NPC474841
0.8261 Intermediate Similarity NPC471446
0.8261 Intermediate Similarity NPC57117
0.8256 Intermediate Similarity NPC178676
0.8229 Intermediate Similarity NPC476081
0.8222 Intermediate Similarity NPC253618
0.8222 Intermediate Similarity NPC206001
0.8222 Intermediate Similarity NPC168131
0.8222 Intermediate Similarity NPC218927
0.8222 Intermediate Similarity NPC77001
0.8193 Intermediate Similarity NPC476601
0.8191 Intermediate Similarity NPC121402
0.8191 Intermediate Similarity NPC175351
0.8191 Intermediate Similarity NPC474921
0.8191 Intermediate Similarity NPC151681
0.8191 Intermediate Similarity NPC224356
0.8191 Intermediate Similarity NPC132753
0.8191 Intermediate Similarity NPC474395
0.8182 Intermediate Similarity NPC189075
0.8182 Intermediate Similarity NPC37628
0.8182 Intermediate Similarity NPC275539
0.8182 Intermediate Similarity NPC52628
0.8172 Intermediate Similarity NPC210214
0.8172 Intermediate Similarity NPC98639
0.8152 Intermediate Similarity NPC166346
0.8152 Intermediate Similarity NPC199543
0.8152 Intermediate Similarity NPC294263
0.8144 Intermediate Similarity NPC99510
0.8144 Intermediate Similarity NPC176883
0.8144 Intermediate Similarity NPC156681
0.8125 Intermediate Similarity NPC111292
0.8125 Intermediate Similarity NPC81530
0.8111 Intermediate Similarity NPC477128
0.8105 Intermediate Similarity NPC473154
0.8105 Intermediate Similarity NPC316598
0.81 Intermediate Similarity NPC474243
0.8095 Intermediate Similarity NPC474433
0.8085 Intermediate Similarity NPC29410
0.8085 Intermediate Similarity NPC256227
0.8085 Intermediate Similarity NPC242848
0.8085 Intermediate Similarity NPC134072
0.8085 Intermediate Similarity NPC200054
0.8085 Intermediate Similarity NPC307164
0.8085 Intermediate Similarity NPC13949
0.8085 Intermediate Similarity NPC104568
0.8085 Intermediate Similarity NPC234993
0.8072 Intermediate Similarity NPC39362
0.8065 Intermediate Similarity NPC477130
0.8065 Intermediate Similarity NPC477129
0.8061 Intermediate Similarity NPC283850
0.8046 Intermediate Similarity NPC123880
0.8046 Intermediate Similarity NPC471159
0.8043 Intermediate Similarity NPC49420
0.8043 Intermediate Similarity NPC250753
0.8041 Intermediate Similarity NPC273005
0.8041 Intermediate Similarity NPC31058
0.8041 Intermediate Similarity NPC136289
0.8041 Intermediate Similarity NPC469606
0.8022 Intermediate Similarity NPC288699
0.8021 Intermediate Similarity NPC476299
0.8021 Intermediate Similarity NPC474012
0.8021 Intermediate Similarity NPC201406
0.8 Intermediate Similarity NPC10864
0.8 Intermediate Similarity NPC476932
0.8 Intermediate Similarity NPC73911
0.798 Intermediate Similarity NPC469607
0.7979 Intermediate Similarity NPC316215
0.7978 Intermediate Similarity NPC476602
0.7978 Intermediate Similarity NPC86316
0.7978 Intermediate Similarity NPC106416
0.7978 Intermediate Similarity NPC329738
0.7978 Intermediate Similarity NPC110405
0.7959 Intermediate Similarity NPC36688
0.7959 Intermediate Similarity NPC120321
0.7959 Intermediate Similarity NPC221421
0.7957 Intermediate Similarity NPC49776
0.7957 Intermediate Similarity NPC470224
0.7957 Intermediate Similarity NPC63118
0.7957 Intermediate Similarity NPC474436
0.7955 Intermediate Similarity NPC22611
0.7955 Intermediate Similarity NPC471037
0.7938 Intermediate Similarity NPC471412
0.7938 Intermediate Similarity NPC303559
0.7935 Intermediate Similarity NPC310479
0.7931 Intermediate Similarity NPC473420
0.7917 Intermediate Similarity NPC28864
0.7917 Intermediate Similarity NPC162459
0.7917 Intermediate Similarity NPC20479
0.7917 Intermediate Similarity NPC478056
0.7917 Intermediate Similarity NPC278386
0.7917 Intermediate Similarity NPC108368
0.7917 Intermediate Similarity NPC252295
0.7917 Intermediate Similarity NPC234617
0.7917 Intermediate Similarity NPC89099
0.7917 Intermediate Similarity NPC471038
0.7917 Intermediate Similarity NPC57079
0.7917 Intermediate Similarity NPC16911
0.7917 Intermediate Similarity NPC38471
0.7917 Intermediate Similarity NPC38296
0.7917 Intermediate Similarity NPC124512
0.7917 Intermediate Similarity NPC98837
0.7917 Intermediate Similarity NPC78427
0.7917 Intermediate Similarity NPC159763
0.7917 Intermediate Similarity NPC23364
0.7917 Intermediate Similarity NPC124703
0.7912 Intermediate Similarity NPC473229
0.79 Intermediate Similarity NPC187435
0.79 Intermediate Similarity NPC67321
0.7889 Intermediate Similarity NPC473226
0.7889 Intermediate Similarity NPC472505
0.7889 Intermediate Similarity NPC12774
0.7889 Intermediate Similarity NPC325594
0.7882 Intermediate Similarity NPC307865
0.7872 Intermediate Similarity NPC66581
0.7872 Intermediate Similarity NPC471720
0.7872 Intermediate Similarity NPC303863
0.7872 Intermediate Similarity NPC47853
0.7872 Intermediate Similarity NPC272635
0.7872 Intermediate Similarity NPC169751
0.7865 Intermediate Similarity NPC159635

  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 NPC305029 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
0.7917 Intermediate Similarity NPD4225 Approved
0.7849 Intermediate Similarity NPD8034 Phase 2
0.7849 Intermediate Similarity NPD8035 Phase 2
0.7778 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1694 Approved
0.7579 Intermediate Similarity NPD6399 Phase 3
0.7551 Intermediate Similarity NPD7638 Approved
0.75 Intermediate Similarity NPD3618 Phase 1
0.7475 Intermediate Similarity NPD7640 Approved
0.7475 Intermediate Similarity NPD7639 Approved
0.7449 Intermediate Similarity NPD7902 Approved
0.7444 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD7748 Approved
0.7292 Intermediate Similarity NPD7515 Phase 2
0.7253 Intermediate Similarity NPD3667 Approved
0.7248 Intermediate Similarity NPD7115 Discovery
0.7245 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD5697 Approved
0.7143 Intermediate Similarity NPD7900 Approved
0.7143 Intermediate Similarity NPD6011 Approved
0.7143 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6899 Approved
0.7143 Intermediate Similarity NPD6881 Approved
0.7115 Intermediate Similarity NPD5739 Approved
0.7115 Intermediate Similarity NPD6675 Approved
0.7115 Intermediate Similarity NPD6402 Approved
0.7115 Intermediate Similarity NPD7128 Approved
0.7113 Intermediate Similarity NPD6079 Approved
0.7103 Intermediate Similarity NPD6649 Approved
0.7103 Intermediate Similarity NPD6650 Approved
0.7097 Intermediate Similarity NPD4786 Approved
0.7083 Intermediate Similarity NPD5328 Approved
0.7079 Intermediate Similarity NPD6116 Phase 1
0.7075 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD6012 Approved
0.7075 Intermediate Similarity NPD6014 Approved
0.7075 Intermediate Similarity NPD6013 Approved
0.7075 Intermediate Similarity NPD6373 Approved
0.7075 Intermediate Similarity NPD6372 Approved
0.7048 Intermediate Similarity NPD5701 Approved
0.7041 Intermediate Similarity NPD4202 Approved
0.7009 Intermediate Similarity NPD6883 Approved
0.7009 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7102 Approved
0.7009 Intermediate Similarity NPD7290 Approved
0.699 Remote Similarity NPD7632 Discontinued
0.6989 Remote Similarity NPD4788 Approved
0.6981 Remote Similarity NPD7320 Approved
0.6981 Remote Similarity NPD6686 Approved
0.6981 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6117 Approved
0.6952 Remote Similarity NPD6008 Approved
0.6947 Remote Similarity NPD7334 Approved
0.6947 Remote Similarity NPD6684 Approved
0.6947 Remote Similarity NPD6409 Approved
0.6947 Remote Similarity NPD7521 Approved
0.6947 Remote Similarity NPD5330 Approved
0.6947 Remote Similarity NPD7146 Approved
0.6944 Remote Similarity NPD6869 Approved
0.6944 Remote Similarity NPD6847 Approved
0.6944 Remote Similarity NPD8130 Phase 1
0.6944 Remote Similarity NPD6617 Approved
0.6932 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6915 Remote Similarity NPD3665 Phase 1
0.6915 Remote Similarity NPD3133 Approved
0.6915 Remote Similarity NPD3666 Approved
0.6881 Remote Similarity NPD8297 Approved
0.6881 Remote Similarity NPD6882 Approved
0.6875 Remote Similarity NPD3573 Approved
0.6832 Remote Similarity NPD5222 Approved
0.6832 Remote Similarity NPD4697 Phase 3
0.6832 Remote Similarity NPD5221 Approved
0.6832 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6827 Remote Similarity NPD5211 Phase 2
0.6818 Remote Similarity NPD8133 Approved
0.6813 Remote Similarity NPD6118 Approved
0.6813 Remote Similarity NPD6114 Approved
0.6813 Remote Similarity NPD6115 Approved
0.6813 Remote Similarity NPD6697 Approved
0.6804 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6804 Remote Similarity NPD6903 Approved
0.6796 Remote Similarity NPD5286 Approved
0.6796 Remote Similarity NPD5285 Approved
0.6796 Remote Similarity NPD4696 Approved
0.6789 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6083 Phase 2
0.6765 Remote Similarity NPD5173 Approved
0.6765 Remote Similarity NPD6084 Phase 2
0.6765 Remote Similarity NPD4755 Approved
0.6733 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6731 Remote Similarity NPD5223 Approved
0.6729 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6699 Remote Similarity NPD5696 Approved
0.6698 Remote Similarity NPD5141 Approved
0.6696 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5225 Approved
0.6667 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD5785 Approved
0.6667 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD5226 Approved
0.6667 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4632 Approved
0.6637 Remote Similarity NPD6317 Approved
0.6635 Remote Similarity NPD4700 Approved
0.6634 Remote Similarity NPD6001 Approved
0.6633 Remote Similarity NPD5737 Approved
0.6633 Remote Similarity NPD6672 Approved
0.6604 Remote Similarity NPD5175 Approved
0.6604 Remote Similarity NPD5174 Approved
0.66 Remote Similarity NPD5693 Phase 1
0.66 Remote Similarity NPD6411 Approved
0.6598 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6579 Remote Similarity NPD6314 Approved
0.6579 Remote Similarity NPD6335 Approved
0.6579 Remote Similarity NPD6313 Approved
0.6569 Remote Similarity NPD5695 Phase 3
0.6566 Remote Similarity NPD1695 Approved
0.6562 Remote Similarity NPD3668 Phase 3
0.6549 Remote Similarity NPD6868 Approved
0.6522 Remote Similarity NPD7101 Approved
0.6522 Remote Similarity NPD7100 Approved
0.6517 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6517 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6009 Approved
0.6489 Remote Similarity NPD7525 Registered
0.6489 Remote Similarity NPD4695 Discontinued
0.6484 Remote Similarity NPD3703 Phase 2
0.6484 Remote Similarity NPD3702 Approved
0.6471 Remote Similarity NPD7507 Approved
0.6466 Remote Similarity NPD6319 Approved
0.6455 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6449 Remote Similarity NPD4754 Approved
0.6436 Remote Similarity NPD5281 Approved
0.6436 Remote Similarity NPD5284 Approved
0.6429 Remote Similarity NPD5279 Phase 3
0.6413 Remote Similarity NPD3701 Clinical (unspecified phase)
0.641 Remote Similarity NPD5983 Phase 2
0.6408 Remote Similarity NPD5210 Approved
0.6408 Remote Similarity NPD4629 Approved
0.64 Remote Similarity NPD5764 Clinical (unspecified phase)
0.64 Remote Similarity NPD6101 Approved
0.64 Remote Similarity NPD4753 Phase 2
0.6395 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6387 Remote Similarity NPD7492 Approved
0.6383 Remote Similarity NPD7645 Phase 2
0.6373 Remote Similarity NPD5779 Approved
0.6373 Remote Similarity NPD5778 Approved
0.6364 Remote Similarity NPD4729 Approved
0.6364 Remote Similarity NPD4730 Approved
0.6364 Remote Similarity NPD5128 Approved
0.6354 Remote Similarity NPD4221 Approved
0.6354 Remote Similarity NPD4223 Phase 3
0.6337 Remote Similarity NPD5207 Approved
0.6337 Remote Similarity NPD46 Approved
0.6337 Remote Similarity NPD6698 Approved
0.6333 Remote Similarity NPD5777 Approved
0.6333 Remote Similarity NPD6616 Approved
0.633 Remote Similarity NPD4767 Approved
0.633 Remote Similarity NPD4768 Approved
0.6327 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6325 Remote Similarity NPD6054 Approved
0.6322 Remote Similarity NPD4224 Phase 2
0.6311 Remote Similarity NPD7319 Approved
0.6304 Remote Similarity NPD7339 Approved
0.6304 Remote Similarity NPD6942 Approved
0.6303 Remote Similarity NPD7604 Phase 2
0.63 Remote Similarity NPD5208 Approved
0.6292 Remote Similarity NPD3698 Phase 2
0.6283 Remote Similarity NPD6053 Discontinued
0.6281 Remote Similarity NPD7078 Approved
0.6277 Remote Similarity NPD3617 Approved
0.6275 Remote Similarity NPD7637 Suspended
0.6273 Remote Similarity NPD6412 Phase 2
0.6271 Remote Similarity NPD6016 Approved
0.6271 Remote Similarity NPD6921 Approved
0.6271 Remote Similarity NPD6909 Approved
0.6271 Remote Similarity NPD6015 Approved
0.6271 Remote Similarity NPD6908 Approved
0.6263 Remote Similarity NPD4519 Discontinued
0.6263 Remote Similarity NPD4623 Approved
0.6263 Remote Similarity NPD6098 Approved
0.6262 Remote Similarity NPD5344 Discontinued
0.625 Remote Similarity NPD4634 Approved
0.625 Remote Similarity NPD5251 Approved
0.625 Remote Similarity NPD5250 Approved
0.625 Remote Similarity NPD5169 Approved
0.625 Remote Similarity NPD6371 Approved
0.625 Remote Similarity NPD5247 Approved
0.625 Remote Similarity NPD5248 Approved
0.625 Remote Similarity NPD5249 Phase 3
0.625 Remote Similarity NPD5135 Approved
0.625 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6238 Remote Similarity NPD6673 Approved
0.6238 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6238 Remote Similarity NPD6904 Approved
0.6238 Remote Similarity NPD6080 Approved
0.6238 Remote Similarity NPD6051 Approved
0.623 Remote Similarity NPD7736 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