NPASS Compound

Natural Product: NPC226981

Natural Product ID	NPC226981
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QYIXCDOBOSTCEI-ILFYRDGGSA-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 76 79 0 0 0 0 0 0 0 0999 V2000 8.3395 0.8352 0.4309 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8748 1.1144 0.4439 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4842 1.7706 -0.8632 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0902 -0.1675 0.5582 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5727 0.1822 0.5672 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8754 -1.1127 0.6805 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3685 -1.1024 0.7695 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0857 -0.2855 2.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6840 -0.5945 -0.4257 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9013 0.8512 -0.7894 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4860 1.4163 -1.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3598 0.4626 -0.3042 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8064 0.4191 -0.7189 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4275 1.7969 -0.7419 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9003 1.5944 -1.0904 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5043 0.8906 0.1220 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0018 0.8727 0.0640 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5169 0.3121 1.3597 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4368 -0.1239 2.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3831 -0.9771 1.6773 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9207 -0.4767 0.3195 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4724 -1.4739 -0.7024 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4521 -0.4975 0.2810 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9046 -1.8940 0.0173 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3946 -1.9161 0.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2493 -0.8914 -0.6391 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0371 -1.1777 -2.1242 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4778 -0.6930 1.1622 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6811 0.1669 1.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8695 1.8168 0.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7039 0.4809 -0.5638 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6409 1.7402 1.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6015 2.4426 -0.6997 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2980 2.3197 -1.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1325 1.0044 -1.6108 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3113 -0.8624 -0.2736 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2524 -0.6982 1.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3974 0.9282 1.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4371 0.6814 -0.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3006 -1.7407 1.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1098 -1.6879 -0.2698 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0671 -2.1448 0.9976 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4826 0.7316 1.9866 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0850 -0.2967 2.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7169 -0.8002 2.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2448 -1.1417 -1.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5206 1.0180 -1.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3209 1.4205 0.0923 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4549 2.4499 -0.6043 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3283 1.5299 -2.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3397 0.6701 0.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9784 -0.0218 -1.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3208 2.2278 0.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9226 2.3801 -1.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4263 2.5482 -1.2179 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9264 0.9428 -1.9907 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2134 1.5037 1.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3921 0.3365 -0.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3258 1.9443 -0.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0794 1.1428 1.8792 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0123 0.7562 2.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9307 -0.7396 3.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5154 -1.0011 2.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7400 -2.0294 1.6375 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5793 -1.5251 -0.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1210 -2.4802 -0.3279 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -1.2747 -1.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0545 -0.2100 1.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3370 -2.5658 0.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1895 -2.2997 -0.9587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0821 -2.9418 -0.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2262 -1.7397 1.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7054 -1.9701 -2.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2297 -0.3076 -2.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9998 -1.5747 -2.5069 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3002 -0.2638 0.7672 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 1 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 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 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 5 39 1 0 6 40 1 0 6 41 1 0 7 42 1 1 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 6 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 1 13 52 1 6 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 1 17 58 1 0 17 59 1 0 18 60 1 1 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 1 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 0 M END

Standard InCHIKey	QYIXCDOBOSTCEI-ILFYRDGGSA-N
Standard InCHI	InChI=1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23+,24+,25+,26+,27-/m1/s1
SMILES	CC(C)CCC[C@@H](C)[C@@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	388.37	Volume:	450.112 ? Van der Waals volume.
Dense:	0.863	LogP:	7.749 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.248 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.306 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	20.0
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:	0.518	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.148	Fsp³:	1.0
MCE-18:	68.37 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.659	Fluc inhibitor:	0.016 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.798	Promiscuous compounds:	0.017

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.032	MDCK Permeability:	-4.976
Pgp-inhibitor:	0.008	Pgp-substrate:	0.022
PAMPA:	0.027 ? 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%):	0.004	30% Bioavailability (F30%):	0.045
50% Bioavailability (F50%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305	MRP1:	0.039
Plasma Protein Binding (PPB):	96.036%	Volume Distribution (VD):	-0.133
Fu:	4.207% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.266
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.654
CYP2C19-inhibitor:	0.952	CYP2C19-substrate:	0.327
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.801
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.494
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.968 ? 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):

13.15

Half-life (T1/2):

0.655

ADMET: Toxicity

hERG Blockers:	0.224	hERG Blockers (10um):	0.429
Human Hepatotoxicity (H-HT):	0.693	Drug-induced Liver Injury (DILI):	0.169
AMES Toxicity:	0.184	Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.631	Skin Sensitization:	0.959
Carcinogencity:	0.898	Eye Corrosion:	0.873
Eye Irritation:	0.995	Respiratory Toxicity:	0.879
Drug-induced Neurotoxicity:	0.025	Ototoxicity:	0.483
Hematotoxicity:	0.364	Drug-induced Nephrotoxicity:	0.501
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.331	Hek293 Cytotoxicity:	0.494
BCF:	2.964 ? 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:	4.587 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.023 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.209 ? 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 NPC226981 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	27493
0.1-0.2	19985
0.2-0.3	2011
0.3-0.4	261
0.4-0.5	79
0.5-0.6	16
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC71460
1.0	High Similarity	NPC218585
0.7556	Intermediate Similarity	NPC148174
0.7209	Intermediate Similarity	NPC114891
0.6471	Remote Similarity	NPC167702
0.6471	Remote Similarity	NPC192456
0.6471	Remote Similarity	NPC280026
0.6383	Remote Similarity	NPC320549
0.6383	Remote Similarity	NPC156277
0.6383	Remote Similarity	NPC58057
0.6383	Remote Similarity	NPC151018
0.6275	Remote Similarity	NPC477820
0.6071	Remote Similarity	NPC323180
0.6	Remote Similarity	NPC254340
0.5957	Remote Similarity	NPC281540
0.5957	Remote Similarity	NPC159654
0.5957	Remote Similarity	NPC167995
0.5957	Remote Similarity	NPC118937
0.5763	Remote Similarity	NPC320478
0.566	Remote Similarity	NPC228994
0.56	Remote Similarity	NPC184819
0.5556	Remote Similarity	NPC141071
0.549	Remote Similarity	NPC327728
0.549	Remote Similarity	NPC6120
0.549	Remote Similarity	NPC131892
0.549	Remote Similarity	NPC213178
0.549	Remote Similarity	NPC103822
0.5273	Remote Similarity	NPC136188
0.5273	Remote Similarity	NPC28657
0.5091	Remote Similarity	NPC244488

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC226981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7848
0.1-0.2	1179
0.2-0.3	80
0.3-0.4	24
0.4-0.5	11
0.5-0.6	5
0.6-0.7	3
0.7-0.8	0
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
0.6471	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4808	Phase 2
0.6383	Remote Similarity	NPD4809	Phase 4
0.549	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.549	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5385	Remote Similarity	NPD4787	Phase 1
0.5273	Remote Similarity	NPD6942	Phase 4
0.5091	Remote Similarity	NPD3671	Phase 1

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