NPASS Compound

Natural Product: NPC12588

Natural Product ID	NPC12588
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QQIOPZFVTIHASB-WUYCRTRWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14537343
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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 75 78 0 0 0 0 0 0 0 0999 V2000 -5.9508 1.4947 0.5252 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8709 0.5533 -0.6196 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2956 0.3797 -1.1846 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3615 -0.8127 -0.3628 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4429 -1.5555 -1.7321 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9196 -0.9554 0.0233 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4935 -0.2660 1.2596 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0203 -0.5177 1.5832 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9066 -2.0159 1.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1308 -0.0875 0.4641 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3127 1.4127 0.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0340 1.8503 -0.5123 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8355 0.6205 -0.5143 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2863 0.9017 -0.4737 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6918 1.4229 -1.8606 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1208 1.9290 -1.6970 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9744 0.9365 -1.0145 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2850 1.0354 -1.1748 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2018 0.0826 -0.5261 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3591 0.3836 -0.2028 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6988 -1.2885 -0.2578 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2230 -1.4168 -0.5594 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4650 -0.1556 -0.1676 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7436 0.1302 1.3115 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0106 -0.4250 -0.3182 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4998 -1.2208 0.8295 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9842 -1.4532 0.7472 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3358 -0.1013 0.7461 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6479 0.6809 1.9852 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9621 2.0291 0.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2342 2.3625 0.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9634 1.0508 1.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3208 1.0597 -1.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2651 0.0975 -2.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8803 -0.3132 -0.5599 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7728 1.3764 -1.0904 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0495 -1.3350 0.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9847 -0.8473 -2.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7955 -2.4493 -1.6904 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4837 -1.7709 -1.9861 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6585 -2.0497 0.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3265 -0.5662 -0.8697 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0643 -0.6390 2.1249 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6822 0.8130 1.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8008 -0.0437 2.5410 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9011 -2.5175 1.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4073 -2.4597 0.8996 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3470 -2.2975 2.6806 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3327 -0.6448 -0.4550 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4603 2.0149 1.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1681 1.5567 -0.5337 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4470 2.6983 -0.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2059 2.1251 -1.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6064 -0.0368 -1.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6261 1.6547 0.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0432 2.2435 -2.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7151 0.5561 -2.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4735 2.1945 -2.7105 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0733 2.8651 -1.1047 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7301 1.8234 -1.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2610 -1.9764 -0.9313 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9260 -1.5570 0.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1237 -1.4954 -1.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8021 -2.3051 -0.0849 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7932 -0.8261 1.8473 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7011 0.6608 1.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9518 0.8115 1.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8157 -0.9981 -1.2507 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6833 -0.7814 1.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9711 -2.2141 0.8093 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7660 -1.9985 1.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7042 -2.0103 -0.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9907 -0.0319 2.7926 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4519 1.4166 1.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2142 1.2125 2.4319 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 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 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 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 28 10 1 0 28 13 1 0 25 14 1 0 23 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 1 5 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 8 45 1 1 9 46 1 0 9 47 1 0 9 48 1 0 10 49 1 6 11 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 6 14 55 1 1 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 18 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 24 65 1 0 24 66 1 0 24 67 1 0 25 68 1 6 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 M END

Standard InCHIKey	QQIOPZFVTIHASB-WUYCRTRWSA-N
Standard InCHI	InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h17-20,23-26H,7-16H2,1-6H3/t19-,20+,23-,24+,25-,26-,27-,28+/m0/s1
SMILES	CC(C)[C@@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	398.35	Volume:	462.136 ? Van der Waals volume.
Dense:	0.862	LogP:	7.004 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.81 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.151 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	17.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.461	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.244	Fsp³:	0.893
MCE-18:	68.264 ? 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:	0.814	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.678	Promiscuous compounds:	0.328

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.048	MDCK Permeability:	-4.82
Pgp-inhibitor:	0.142	Pgp-substrate:	0.001
PAMPA:	0.002 ? 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%):	0.029	30% Bioavailability (F30%):	0.375
50% Bioavailability (F50%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233	MRP1:	0.029
Plasma Protein Binding (PPB):	95.725%	Volume Distribution (VD):	-0.068
Fu:	4.289% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.482
BSEP inhibitor:	0.528

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.038	CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

12.88

Half-life (T1/2):

0.255

ADMET: Toxicity

hERG Blockers:	0.182	hERG Blockers (10um):	0.572
Human Hepatotoxicity (H-HT):	0.758	Drug-induced Liver Injury (DILI):	0.313
AMES Toxicity:	0.169	Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.373	Skin Sensitization:	0.947
Carcinogencity:	0.905	Eye Corrosion:	0.751
Eye Irritation:	0.98	Respiratory Toxicity:	0.681
Drug-induced Neurotoxicity:	0.292	Ototoxicity:	0.403
Hematotoxicity:	0.65	Drug-induced Nephrotoxicity:	0.589
Genotoxicity:	0.054	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.311	Hek293 Cytotoxicity:	0.483
BCF:	3.279 ? 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:	4.871 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.34 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.818 ? 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
NPO15284	Periconia byssoides	Species	Periconiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21391658]
NPO13364	Caloncoba glauca	Species	Achariaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22360639]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO13364	Caloncoba glauca	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15284	Periconia byssoides	Species	Periconiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9161	Celastrus pringlei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3857	Perezia multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11120.1	Brassica rapa subsp. chinensis	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11120.1	Brassica rapa subsp. chinensis	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11120.1	Brassica rapa subsp. chinensis	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO11120.1	Brassica rapa subsp. chinensis	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18888	Goniothalamus sesquipedalis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6577	Spongia equina	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18960	Lophanthera lactescens	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7102	Reniera sarai	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3857	Perezia multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19405	Hovea acutifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18726	Spatholobus roxburghii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17971	Coryphantha vivipara	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9161	Celastrus pringlei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11120.1	Brassica rapa subsp. chinensis	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14764	Ehretia laevis	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26037	Linaria genistifolia	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16663	Malus orientalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16004	Phyllotopsis nidulans	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14405	Randia siamensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17836	Ostrea edulis	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15284	Periconia byssoides	Species	Periconiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15821	Apis dorsata	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13364	Caloncoba glauca	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13496	Mentzelia lindleyi	Species	Loasaceae	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 NPC12588 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	21182
0.1-0.2	25021
0.2-0.3	3340
0.3-0.4	227
0.4-0.5	47
0.5-0.6	24
0.6-0.7	5
0.7-0.8	1
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8913	High Similarity	NPC149203
0.8478	Intermediate Similarity	NPC282593
0.8298	Intermediate Similarity	NPC35734
0.8298	Intermediate Similarity	NPC159577
0.8298	Intermediate Similarity	NPC602429
0.7551	Intermediate Similarity	NPC115023
0.7447	Intermediate Similarity	NPC307176
0.7447	Intermediate Similarity	NPC321874
0.7222	Intermediate Similarity	NPC320514
0.7059	Intermediate Similarity	NPC237712
0.7	Intermediate Similarity	NPC214043
0.7	Intermediate Similarity	NPC85774
0.6923	Remote Similarity	NPC249312
0.6296	Remote Similarity	NPC303613
0.62	Remote Similarity	NPC139397
0.6071	Remote Similarity	NPC469948
0.6038	Remote Similarity	NPC255021
0.5962	Remote Similarity	NPC2634
0.5962	Remote Similarity	NPC265782
0.5962	Remote Similarity	NPC251929
0.5862	Remote Similarity	NPC309603
0.5741	Remote Similarity	NPC227064
0.5741	Remote Similarity	NPC474228
0.5741	Remote Similarity	NPC329043
0.5741	Remote Similarity	NPC58841
0.5741	Remote Similarity	NPC161423
0.5714	Remote Similarity	NPC323765
0.5636	Remote Similarity	NPC144258
0.5636	Remote Similarity	NPC327115
0.5614	Remote Similarity	NPC310010
0.5614	Remote Similarity	NPC326627
0.5439	Remote Similarity	NPC20610
0.5312	Remote Similarity	NPC187159
0.5263	Remote Similarity	NPC247325
0.5263	Remote Similarity	NPC328539
0.5254	Remote Similarity	NPC473999
0.5254	Remote Similarity	NPC185936
0.5254	Remote Similarity	NPC168027
0.5246	Remote Similarity	NPC489872
0.5161	Remote Similarity	NPC305039
0.5161	Remote Similarity	NPC205860

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC12588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6672
0.1-0.2	2207
0.2-0.3	183
0.3-0.4	54
0.4-0.5	15
0.5-0.6	14
0.6-0.7	4
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
0.7447	Intermediate Similarity	NPD4747	Phase 4
0.6364	Remote Similarity	NPD5737	Phase 4
0.6182	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6939	Phase 3
0.614	Remote Similarity	NPD6672	Phase 4
0.5962	Remote Similarity	NPD4691	Approved
0.5741	Remote Similarity	NPD3666	Phase 4
0.5741	Remote Similarity	NPD4221	Phase 4
0.569	Remote Similarity	NPD6409	Approved
0.5614	Remote Similarity	NPD4753	Phase 2
0.5614	Remote Similarity	NPD5330	Phase 4
0.5439	Remote Similarity	NPD4693	Phase 3
0.541	Remote Similarity	NPD6083	Phase 4
0.541	Remote Similarity	NPD6084	Phase 2
0.5161	Remote Similarity	NPD6684	Phase 4
0.5161	Remote Similarity	NPD6904	Phase 4
0.5161	Remote Similarity	NPD7334	Approved
0.5161	Remote Similarity	NPD7521	Phase 4
0.5079	Remote Similarity	NPD6903	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