NPASS Compound

Natural Product: NPC64377

Natural Product ID	NPC64377
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UPGTYLFCVNHBTN-KKZXZXIDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 72 75 0 0 0 0 0 0 0 0999 V2000 -6.2843 0.2729 2.0022 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8121 0.6693 0.6355 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5164 2.0060 0.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5908 0.8582 -0.2630 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7868 -0.3565 -0.3858 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5158 -0.3779 -0.0041 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6632 -1.5835 -0.1093 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4258 -2.2404 1.2254 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5066 -1.3947 -0.9629 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6330 -2.6588 -1.0489 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3712 -2.1750 -2.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5892 -0.7068 -1.6795 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0095 -0.4832 -1.3029 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5973 0.5055 -2.2848 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8623 1.1199 -1.8543 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3318 1.1016 -0.6272 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6407 1.7567 -0.2649 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5326 0.7318 0.3420 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9038 -0.6254 0.4747 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5200 -0.6471 0.9952 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6076 0.4375 0.4426 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4499 1.4253 1.6096 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2470 -0.0928 0.1210 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1353 0.7926 0.6535 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0753 -0.1459 0.6731 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4929 -0.3381 -0.7267 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1095 0.9978 -1.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1091 1.0791 1.5455 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0888 -0.8324 1.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0241 0.4939 2.8005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3376 0.8311 2.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5131 -0.0649 0.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6069 1.8517 0.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2476 2.6180 -0.1532 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1867 2.5017 1.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0296 1.7055 0.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9872 1.1830 -1.2624 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2269 -1.2550 -0.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1406 0.5612 0.4086 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3056 -2.3495 -0.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4017 -2.6437 1.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1087 -1.4877 1.9756 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7730 -3.1169 1.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8723 -1.2514 -2.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -3.5202 -1.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1679 -2.8078 -0.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0634 -2.3134 -3.0535 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3119 -2.7507 -1.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3559 -0.1622 -2.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5682 -1.4290 -1.4730 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8882 1.3721 -2.4516 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6890 0.0648 -3.3084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4887 1.6454 -2.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4711 2.6476 0.3566 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0640 2.1672 -1.2292 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4035 0.5870 -0.3673 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0114 -1.1780 -0.5044 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5442 -1.2061 1.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4885 -0.6873 2.0995 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0475 -1.6171 0.6611 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1193 0.8709 2.5143 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8731 2.3079 1.3530 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4807 1.7699 1.8603 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1540 -1.0241 0.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3050 1.0660 1.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9586 1.6835 0.0564 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8383 0.4059 1.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2746 -1.0650 1.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0751 0.8713 -1.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2107 1.7030 -0.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4486 1.4480 -1.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8869 0.4779 1.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 18 28 1 0 26 9 1 0 26 12 1 0 23 13 1 0 21 16 1 0 1 29 1 0 1 30 1 0 1 31 1 0 2 32 1 0 3 33 1 0 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 6 39 1 0 7 40 1 6 8 41 1 0 8 42 1 0 8 43 1 0 9 44 1 6 10 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 6 13 50 1 6 14 51 1 0 14 52 1 0 15 53 1 0 17 54 1 0 17 55 1 0 18 56 1 6 19 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 22 61 1 0 22 62 1 0 22 63 1 0 23 64 1 1 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 M END

Standard InCHIKey	UPGTYLFCVNHBTN-KKZXZXIDSA-N
Standard InCHI	InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6,8-9,18-19,21-25,28H,7,10-17H2,1-5H3/b8-6+/t19-,21-,22+,23-,24+,25-,26-,27+/m0/s1
SMILES	CC(C)C/C=C/[C@H](C)[C@@H]1CC[C@@H]2[C@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	384.34	Volume:	444.84 ? Van der Waals volume.
Dense:	0.864	LogP:	6.721 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.93 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.487 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.51	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.426	Fsp³:	0.852
MCE-18:	67.6 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.965	Fluc inhibitor:	0.01 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.718	Promiscuous compounds:	0.009

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.008	MDCK Permeability:	-4.758
Pgp-inhibitor:	0.999	Pgp-substrate:	0.002
PAMPA:	0.005 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.234	30% Bioavailability (F30%):	0.41
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.797
Plasma Protein Binding (PPB):	98.403%	Volume Distribution (VD):	-0.189
Fu:	1.407% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.238
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.03	CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.254	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.965 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

13.425

Half-life (T1/2):

0.628

ADMET: Toxicity

hERG Blockers:	0.118	hERG Blockers (10um):	0.453
Human Hepatotoxicity (H-HT):	0.605	Drug-induced Liver Injury (DILI):	0.181
AMES Toxicity:	0.099	Rat Oral Acute Toxicity:	0.222
Maximum Recommended Daily Dose:	0.666	Skin Sensitization:	0.917
Carcinogencity:	0.785	Eye Corrosion:	0.167
Eye Irritation:	0.78	Respiratory Toxicity:	0.735
Drug-induced Neurotoxicity:	0.146	Ototoxicity:	0.599
Hematotoxicity:	0.292	Drug-induced Nephrotoxicity:	0.468
Genotoxicity:	0.011	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.423	Hek293 Cytotoxicity:	0.569
BCF:	2.65 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.134 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.946 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.75 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10075800]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10650102]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	Mandapam Coast, Tamilnadu, India	n.a.	PMID[22704923]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9463111]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC64377 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	22853
0.1-0.2	23537
0.2-0.3	3079
0.3-0.4	248
0.4-0.5	74
0.5-0.6	18
0.6-0.7	30
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC154330
0.7843	Intermediate Similarity	NPC113733
0.76	Intermediate Similarity	NPC162742
0.76	Intermediate Similarity	NPC304309
0.76	Intermediate Similarity	NPC470228
0.7451	Intermediate Similarity	NPC600590
0.7407	Intermediate Similarity	NPC33913
0.7308	Intermediate Similarity	NPC136188
0.7308	Intermediate Similarity	NPC28657
0.7115	Intermediate Similarity	NPC22105
0.7115	Intermediate Similarity	NPC34019
0.7115	Intermediate Similarity	NPC107059
0.7037	Intermediate Similarity	NPC264245
0.6981	Remote Similarity	NPC474216
0.6909	Remote Similarity	NPC328714
0.6852	Remote Similarity	NPC230301
0.6852	Remote Similarity	NPC198968
0.6852	Remote Similarity	NPC285893
0.6852	Remote Similarity	NPC134847
0.6792	Remote Similarity	NPC221758
0.6786	Remote Similarity	NPC318495
0.6727	Remote Similarity	NPC241290
0.6727	Remote Similarity	NPC164840
0.6727	Remote Similarity	NPC484739
0.6727	Remote Similarity	NPC209944
0.6727	Remote Similarity	NPC155986
0.6607	Remote Similarity	NPC321381
0.6552	Remote Similarity	NPC243985
0.6552	Remote Similarity	NPC280710
0.6552	Remote Similarity	NPC240650
0.6491	Remote Similarity	NPC472265
0.6491	Remote Similarity	NPC59453
0.6441	Remote Similarity	NPC47761
0.6429	Remote Similarity	NPC51014
0.6379	Remote Similarity	NPC603646
0.6271	Remote Similarity	NPC473943
0.6271	Remote Similarity	NPC155011
0.6167	Remote Similarity	NPC474164
0.6167	Remote Similarity	NPC488870
0.6154	Remote Similarity	NPC96319
0.6129	Remote Similarity	NPC601043
0.6129	Remote Similarity	NPC605412
0.6071	Remote Similarity	NPC328313
0.5932	Remote Similarity	NPC50964
0.5833	Remote Similarity	NPC477522
0.569	Remote Similarity	NPC76879
0.5667	Remote Similarity	NPC1272
0.5667	Remote Similarity	NPC470614
0.5614	Remote Similarity	NPC151519
0.5517	Remote Similarity	NPC20688
0.5469	Remote Similarity	NPC474349
0.5469	Remote Similarity	NPC474189
0.5333	Remote Similarity	NPC234193
0.5323	Remote Similarity	NPC58063
0.5303	Remote Similarity	NPC5985
0.5246	Remote Similarity	NPC87604
0.5211	Remote Similarity	NPC3715
0.5152	Remote Similarity	NPC176012
0.5072	Remote Similarity	NPC235126
0.5072	Remote Similarity	NPC309493
0.5072	Remote Similarity	NPC242419

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC64377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7636
0.1-0.2	1345
0.2-0.3	135
0.3-0.4	27
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7308	Intermediate Similarity	NPD6942	Phase 4
0.6852	Remote Similarity	NPD7339	Approved
0.6792	Remote Similarity	NPD4786	Phase 1
0.6154	Remote Similarity	NPD3701	Pre-clinical
0.5614	Remote Similarity	NPD3667	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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