NPASS Compound

Natural Product: NPC20012

Natural Product ID	NPC20012
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HVYWMOMLDIMFJA-KPCFCYOOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	124909224
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 74 77 0 0 0 0 0 0 0 0999 V2000 -5.5229 -1.9489 -0.4121 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4137 -0.7256 -0.4550 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8061 -1.0624 0.0462 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7592 0.3315 0.3982 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3749 0.5938 -0.2377 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7249 1.6385 0.6043 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3499 2.0794 0.1495 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8898 3.1210 1.1172 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5181 0.9248 -0.0948 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2987 0.0048 1.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5713 -1.1253 0.3509 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1605 -0.4759 -0.7778 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6051 -0.8250 -0.7834 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3255 -0.3723 -2.0193 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7977 -0.4037 -1.8702 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4551 -0.5051 -0.7498 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9426 -0.5330 -0.6463 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4472 -1.6361 0.2284 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5017 -2.3090 1.1121 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0651 -2.0086 1.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7461 -0.6061 0.5285 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3627 0.3215 1.5874 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2726 -0.3649 0.4881 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8698 1.0074 0.9004 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9011 1.7306 0.0537 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1553 1.0064 -0.6593 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3187 1.5981 -2.0787 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5539 -1.1133 0.9414 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1300 -2.8595 -0.4036 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8170 -1.8935 -1.2736 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8840 -1.9629 0.5133 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5414 -0.3417 -1.4874 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3693 -0.1459 0.2991 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6687 -1.7055 0.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3740 -1.5830 -0.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3708 1.2512 0.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6708 0.0364 1.4522 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5907 1.0143 -1.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8277 -0.3701 -0.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3984 2.5463 0.5305 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7404 1.3994 1.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5567 2.6307 -0.8031 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4187 2.7253 2.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8354 3.6205 1.4980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3575 3.9825 0.6569 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0675 0.2748 -0.8283 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7340 0.4309 1.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2396 -0.4402 1.4734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0077 -1.7588 1.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3423 -1.8179 -0.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2619 -0.7875 -1.7729 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6524 -1.9412 -0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0998 -1.0392 -2.9024 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0397 0.6395 -2.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4143 -0.3363 -2.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3259 -0.5833 -1.6875 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2365 0.4776 -0.2713 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9303 -2.3875 -0.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6105 -3.4341 1.0171 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8266 -2.1346 2.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5398 -2.7769 0.4001 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5674 -2.0848 2.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7976 1.2260 1.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6392 0.5011 2.4079 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2358 -0.1868 2.0963 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8678 -1.0514 1.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5615 1.0634 1.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8219 1.6235 0.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5447 2.5913 0.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5101 2.2933 -0.7272 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3184 2.0424 -2.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4136 2.3959 -2.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2904 0.7708 -2.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8594 -0.2567 0.5528 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 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 5 39 1 0 6 40 1 0 6 41 1 0 7 42 1 6 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 6 13 52 1 1 14 53 1 0 14 54 1 0 15 55 1 0 17 56 1 0 17 57 1 0 18 58 1 6 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 22 63 1 0 22 64 1 0 22 65 1 0 23 66 1 1 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 M END

Standard InCHIKey	HVYWMOMLDIMFJA-KPCFCYOOSA-N
Standard InCHI	InChI=1S/C27H46O/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/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,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=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	386.35	Volume:	447.476 ? Van der Waals volume.
Dense:	0.863	LogP:	7.28 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.171 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.515 ? 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:	0.488	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.163	Fsp³:	0.926
MCE-18:	67.0 ? 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:	0.899	Fluc inhibitor:	0.016 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.741	Promiscuous compounds:	0.01

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.985	MDCK Permeability:	-4.941
Pgp-inhibitor:	0.728	Pgp-substrate:	0.053
PAMPA:	0.037 ? 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%):	0.011	30% Bioavailability (F30%):	0.111
50% Bioavailability (F50%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.38	MRP1:	0.605
Plasma Protein Binding (PPB):	97.451%	Volume Distribution (VD):	-0.171
Fu:	2.883% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.332
BSEP inhibitor:	0.418

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.96	CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.777 ? 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):

12.582

Half-life (T1/2):

0.451

ADMET: Toxicity

hERG Blockers:	0.147	hERG Blockers (10um):	0.472
Human Hepatotoxicity (H-HT):	0.611	Drug-induced Liver Injury (DILI):	0.117
AMES Toxicity:	0.195	Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.61	Skin Sensitization:	0.951
Carcinogencity:	0.811	Eye Corrosion:	0.419
Eye Irritation:	0.915	Respiratory Toxicity:	0.632
Drug-induced Neurotoxicity:	0.081	Ototoxicity:	0.52
Hematotoxicity:	0.181	Drug-induced Nephrotoxicity:	0.354
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.35	Hek293 Cytotoxicity:	0.365
BCF:	2.915 ? 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:	4.486 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.041 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.129 ? 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]
NPO1241	Laetia procera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16168652]
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]
NPO17213	Carya illinoinensis	Species	Juglandaceae	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]
NPO16204	Zieria chevalieri	Species	Rutaceae	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]
NPO17213	Carya illinoinensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17213	Carya illinoinensis	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6452	Taraxacum obovatum	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]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6452	Taraxacum obovatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17213	Carya illinoinensis	Species	Juglandaceae	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]
NPO17213	Carya illinoinensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6452	Taraxacum obovatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1241	Laetia procera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	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]
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]

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 NPC20012 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	23287
0.1-0.2	22487
0.2-0.3	3664
0.3-0.4	255
0.4-0.5	78
0.5-0.6	28
0.6-0.7	24
0.7-0.8	1
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC136188
1.0	High Similarity	NPC28657
0.86	High Similarity	NPC321381
0.84	Intermediate Similarity	NPC155986
0.8333	Intermediate Similarity	NPC162742
0.8333	Intermediate Similarity	NPC304309
0.8333	Intermediate Similarity	NPC470228
0.8163	Intermediate Similarity	NPC22105
0.8163	Intermediate Similarity	NPC34019
0.8163	Intermediate Similarity	NPC107059
0.8	Intermediate Similarity	NPC474216
0.7843	Intermediate Similarity	NPC230301
0.7843	Intermediate Similarity	NPC198968
0.7843	Intermediate Similarity	NPC285893
0.7843	Intermediate Similarity	NPC134847
0.7692	Intermediate Similarity	NPC241290
0.7692	Intermediate Similarity	NPC164840
0.7692	Intermediate Similarity	NPC484739
0.7692	Intermediate Similarity	NPC209944
0.7451	Intermediate Similarity	NPC600590
0.7407	Intermediate Similarity	NPC59453
0.7358	Intermediate Similarity	NPC264245
0.7273	Intermediate Similarity	NPC603646
0.7143	Intermediate Similarity	NPC473943
0.7091	Intermediate Similarity	NPC472265
0.7091	Intermediate Similarity	NPC318495
0.7018	Intermediate Similarity	NPC488870
0.6981	Remote Similarity	NPC154330
0.6852	Remote Similarity	NPC113733
0.6842	Remote Similarity	NPC243985
0.6842	Remote Similarity	NPC280710
0.6842	Remote Similarity	NPC155011
0.6792	Remote Similarity	NPC221758
0.6724	Remote Similarity	NPC47761
0.6667	Remote Similarity	NPC109546
0.6667	Remote Similarity	NPC317458
0.6667	Remote Similarity	NPC47982
0.6607	Remote Similarity	NPC328714
0.6607	Remote Similarity	NPC31564
0.6552	Remote Similarity	NPC240650
0.6491	Remote Similarity	NPC33913
0.6441	Remote Similarity	NPC474164
0.6429	Remote Similarity	NPC51014
0.6207	Remote Similarity	NPC153987
0.6182	Remote Similarity	NPC244488
0.6154	Remote Similarity	NPC96319
0.6129	Remote Similarity	NPC601043
0.6129	Remote Similarity	NPC605412
0.6102	Remote Similarity	NPC477522
0.6071	Remote Similarity	NPC328313
0.6034	Remote Similarity	NPC87604
0.5789	Remote Similarity	NPC183927
0.5667	Remote Similarity	NPC1272
0.5667	Remote Similarity	NPC470614
0.5614	Remote Similarity	NPC151519
0.5593	Remote Similarity	NPC23852
0.5593	Remote Similarity	NPC317927
0.5517	Remote Similarity	NPC20688
0.5439	Remote Similarity	NPC81306
0.5424	Remote Similarity	NPC76879
0.5323	Remote Similarity	NPC474752
0.5323	Remote Similarity	NPC474683
0.5303	Remote Similarity	NPC5985
0.5273	Remote Similarity	NPC71460
0.5273	Remote Similarity	NPC218585
0.5246	Remote Similarity	NPC145879
0.5238	Remote Similarity	NPC270155
0.5231	Remote Similarity	NPC474970
0.5231	Remote Similarity	NPC474349
0.5211	Remote Similarity	NPC3715
0.5167	Remote Similarity	NPC84694
0.5167	Remote Similarity	NPC28862
0.5167	Remote Similarity	NPC143182
0.5152	Remote Similarity	NPC176012
0.5085	Remote Similarity	NPC228994
0.5072	Remote Similarity	NPC264127
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 NPC20012 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	126
0.3-0.4	30
0.4-0.5	8
0.5-0.6	1
0.6-0.7	2
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6942	Phase 4
0.7843	Intermediate 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